4-Amino-5-ethylsulfonyl-2-methoxybenzoic acid supplier

Name
4-Amino-5-ethylsulfonyl-2-methoxybenzoic acid
EINECS 275-833-8
CAS No. 71675-87-1
Article Data3
CAS DataBase
Density 1.39 g/cm³
Solubility 8.555g/L at 25℃
Melting Point 82-85 °C
Formula C₁₀H₁₃NO₅S
Boiling Point 529.6 °C at 760 mmHg
Molecular Weight 259.283
Flash Point 274.1 °C
Transport Information
Appearance Slightly pink solid
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 4-Amino-5-(ethylsulphonyl)-o-anisic acid;
PSA 115.07000
LogP 2.43120

Synthetic route

: 1119455-01-4
methyl 4-amino-5-(ethylthio)-2-methoxybenzoate

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

Conditions

Conditions	Yield
Stage #1: methyl 4-amino-5-(ethylthio)-2-methoxybenzoate With dihydrogen peroxide; sodium tungstate In isopropyl alcohol at 40 - 45℃; Industry scale; Stage #2: With water; sodium hydroxide In isopropyl alcohol at 60 - 65℃; Industry scale; Stage #3: With hydrogenchloride In water; isopropyl alcohol pH=4 - 4.5; Industry scale;	82%
Multi-step reaction with 2 steps 1.1: sodium hydroxide; water / methanol / 65 °C / Industry scale 1.2: 5 - 10 °C / pH 4 - 4.5 / Industry scale 2.1: dihydrogen peroxide / sodium tungstate / water; methanol / 5 h / 20 - 30 °C View Scheme

: 2-methoxy-4-amino-5-ethylthio benzoic acid

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

Conditions

Conditions	Yield
With dihydrogen peroxide; sodium tungstate In methanol; water at 20 - 30℃; for 5h; Product distribution / selectivity;	80%

: 27492-84-8
Methyl 4-amino-2-methoxybenzoate

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: bromine / methanol / 5 - 15 °C / Industry scale 2.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale 3.1: sodium hydroxide; water / methanol / 65 °C / Industry scale 3.2: 5 - 10 °C / pH 4 - 4.5 / Industry scale 4.1: dihydrogen peroxide / sodium tungstate / water; methanol / 5 h / 20 - 30 °C View Scheme
Multi-step reaction with 3 steps 1.1: bromine / methanol / 5 - 15 °C / Industry scale 2.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale 3.1: dihydrogen peroxide / sodium tungstate / isopropyl alcohol / 40 - 45 °C / Industry scale 3.2: 60 - 65 °C / Industry scale 3.3: pH 4 - 4.5 / Industry scale View Scheme

: 65-49-6
4-Aminosalicylic acid

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: potassium hydroxide; tetrabutylammomium bromide / acetone / 1 h / 25 - 35 °C / Industry scale 2.1: bromine / methanol / 5 - 15 °C / Industry scale 3.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale 4.1: sodium hydroxide; water / methanol / 65 °C / Industry scale 4.2: 5 - 10 °C / pH 4 - 4.5 / Industry scale 5.1: dihydrogen peroxide / sodium tungstate / water; methanol / 5 h / 20 - 30 °C View Scheme
Multi-step reaction with 4 steps 1.1: potassium hydroxide; tetrabutylammomium bromide / acetone / 1 h / 25 - 35 °C / Industry scale 2.1: bromine / methanol / 5 - 15 °C / Industry scale 3.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale 4.1: dihydrogen peroxide / sodium tungstate / isopropyl alcohol / 40 - 45 °C / Industry scale 4.2: 60 - 65 °C / Industry scale 4.3: pH 4 - 4.5 / Industry scale View Scheme

Yield

Multi-step reaction with 5 steps
1.1: potassium hydroxide; tetrabutylammomium bromide / acetone / 1 h / 25 - 35 °C / Industry scale
2.1: bromine / methanol / 5 - 15 °C / Industry scale
3.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale
4.1: sodium hydroxide; water / methanol / 65 °C / Industry scale
4.2: 5 - 10 °C / pH 4 - 4.5 / Industry scale
5.1: dihydrogen peroxide / sodium tungstate / water; methanol / 5 h / 20 - 30 °C
View Scheme

Multi-step reaction with 4 steps
1.1: potassium hydroxide; tetrabutylammomium bromide / acetone / 1 h / 25 - 35 °C / Industry scale
2.1: bromine / methanol / 5 - 15 °C / Industry scale
3.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale
4.1: dihydrogen peroxide / sodium tungstate / isopropyl alcohol / 40 - 45 °C / Industry scale
4.2: 60 - 65 °C / Industry scale
4.3: pH 4 - 4.5 / Industry scale
View Scheme

: 59168-56-8
methyl 4-amino-2-methoxy-5-thiocyanatobenzoate

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale 2.1: sodium hydroxide; water / methanol / 65 °C / Industry scale 2.2: 5 - 10 °C / pH 4 - 4.5 / Industry scale 3.1: dihydrogen peroxide / sodium tungstate / water; methanol / 5 h / 20 - 30 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale 2.1: dihydrogen peroxide / sodium tungstate / isopropyl alcohol / 40 - 45 °C / Industry scale 2.2: 60 - 65 °C / Industry scale 2.3: pH 4 - 4.5 / Industry scale View Scheme

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: 168828-90-8
(S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine

: 1390617-35-2
4-amino-5-(ethylsulfonyl)-N-(S)-[[3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxooxazolidin-5-yl]methyl]-2-methoxybenzamide

Conditions

Conditions	Yield
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at 0 - 20℃; for 0.5h; Stage #2: (S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine In dichloromethane at 0 - 20℃; for 4h;	93%

: 26116-12-1
1-ethyl-2-pyrrolidinemethanamine

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: 71675-85-9
amisulpride

Conditions

Conditions	Yield
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 10 - 20℃; for 1.5h; Stage #2: 1-ethyl-2-pyrrolidinemethanamine With triethylamine In acetonitrile at 80℃; for 2h;	86.8%
With C36H24B4N2O3 In toluene for 14h; Molecular sieve; Reflux; chemoselective reaction;	76%
With chloroformic acid ethyl ester; triethylamine In acetone at 0 - 30℃;	70%

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: 541-41-3
chloroformic acid ethyl ester

: (-)-Amisulpride

Conditions

Conditions	Yield
In acetone	84%

...Expand

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: C20H24N2O9S2

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25 - 40℃; for 12h; Reagent/catalyst; Solvent;	72.52%

: 1-allyl 2-aminoethylpyrrolidine

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: 541-41-3
chloroformic acid ethyl ester

: 71675-89-3
N-[1-allyl 2-pyrrolidylmethyl] 2-methoxy 4-amino 5-ethylsulphonyl benzamide

Conditions

Conditions	Yield
With hydrogenchloride; triethylamine In water; acetone	67%

...Expand

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: 541-41-3
chloroformic acid ethyl ester

: 71820-57-0
(-)-(S)-2-Aminomethyl-1(cyclopropylmethyl)pyrrolidine

: 72135-20-7
LUR 2366

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran; water	66.5%

...Expand

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: 148516-65-8
4-amino-5-(ethylsulfonyl)-2-hydroxybenzoic acid

Conditions

Conditions	Yield
With boron tribromide In dichloromethane at -50 - 20℃;	65%

: 26116-12-1
1-ethyl-2-pyrrolidinemethanamine

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: 541-41-3
chloroformic acid ethyl ester

: 71675-85-9
amisulpride

Conditions

Conditions	Yield
With triethylamine In water; acetone	61%

...Expand

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: 1-ethyl-2-aminomethylpyrrolidine hydrochloride

: 71675-85-9
amisulpride

Conditions

Conditions	Yield
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.5h; Stage #2: 1-ethyl-2-aminomethylpyrrolidine hydrochloride With triethylamine In dichloromethane at 20℃;	29.7%

: 1-cyclohexylmethyl-pyrrolidin-3-R-ylamine

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: 543-27-1
isobutyl chloroformate

A: 55-21-0
benzamide

B: 72135-95-6
N-(1-cyclohexylmethyl-3-pyrrolidinyl)-2-methoxy-4-amino-5-ethyl-sulphonyl-benzamide

Conditions

Conditions	Yield
With triethylamine In water; ethyl acetate; acetone

...Expand

: 1-cyclopropylmethyl-3-aminopyrrolidine

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: 543-27-1
isobutyl chloroformate

: 72135-94-5
N-(1-cyclopropylmethyl-3-pyrrolidinyl)-2-methoxy-4-amino-5-ethyl-sulphonyl-benzamide

Conditions

Conditions	Yield
With triethylamine In water; acetone; Diethyl carbonate

...Expand

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: 554-68-7
triethylamine hydrochloride

Conditions

Conditions	Yield
With triethylamine In acetone

: 26171-06-2
1-methyl-2-aminomethyl-pyrrolidine

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: 541-41-3
chloroformic acid ethyl ester

: 71675-88-2, 71675-93-9
N-(1-methyl-2-pyrrolidylmethyl)-2-methoxy-4-amino-5-ethylsulphonylbenzamid

Conditions

Conditions	Yield
With triethylamine In water; acetone

...Expand

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: 22795-97-7
(R)-2-aminomethyl-1-ethylpyrrolidine

: 108-23-6
isopropyl chloroformate

: (R)-(+)-4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide

Conditions

Conditions	Yield
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid; isopropyl chloroformate With triethylamine In acetone at 5℃; for 0.5h; Stage #2: (R)-2-aminomethyl-1-ethylpyrrolidine In acetone at 0 - 20℃; for 1.5h;

...Expand

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: R-amisulpride maleic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine / acetone / 0.5 h / 5 °C 1.2: 1.5 h / 0 - 20 °C 2.1: methanol / 5 h / 45 °C View Scheme

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: (R)-(+)-4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide L-tartrate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine / acetone / 0.5 h / 5 °C 1.2: 1.5 h / 0 - 20 °C 2.1: methanol / 2 h / 40 - 45 °C View Scheme

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: R-amisulpride hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine / acetone / 0.5 h / 5 °C 1.2: 1.5 h / 0 - 20 °C 2.1: hydrogenchloride / water; methanol; diethyl ether / 2 h / 20 °C View Scheme

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: (S)-N-(2,4-dimethoxybenzyl)-4-amino-N-((1-ethylpyrrolidin-2-yl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine / acetone / 0.25 h / 0 - 10 °C / Inert atmosphere 1.2: 1.5 h / -5 - 5 °C 2.1: acetone / 4 h / 0 - 20 °C View Scheme

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: (-)-Amisulpride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / acetone / 0.25 h / 0 - 10 °C / Inert atmosphere 1.2: 1.5 h / -5 - 5 °C 2.1: acetone / 4 h / 0 - 20 °C 3.1: hydrogenchloride / methanol; water / 2 h / 20 °C View Scheme

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: 3282-30-2
pivaloyl chloride

: 4-amino-2-methoxy-5-ethylsulfonyl benzoate pivalic anhydride

Conditions

Conditions	Yield
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With triethylamine In acetone at 0 - 10℃; for 0.25h; Inert atmosphere; Stage #2: pivaloyl chloride In acetone at -5 - 5℃; for 1.5h;

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: (-)-Amisulpride

Conditions

Conditions	Yield
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In acetone at -10℃; for 1h; Inert atmosphere; Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In acetone at -10 - 20℃; Temperature; Reagent/catalyst; Inert atmosphere;	49 g
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In acetone at -8 - 0℃; Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In acetone at 0 - 20℃; Temperature;
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In acetone at -10℃; for 1h; Stage #2: (S)-2-(Aminomethyl)-1-ethylpyrrolidine In tert-butyl methyl ether; ethyl acetate; acetone for 2h;
With 4-methyl-morpholine; chloroformic acid ethyl ester In acetone at -8 - 20℃; Inert atmosphere;

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: 22795-99-9
(S)-2-(Aminomethyl)-1-ethylpyrrolidine

: (S)-(-)-4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide D-tartrate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine; chloroformic acid ethyl ester / acetone / 1 h / -10 °C / Inert atmosphere 1.2: -10 - 20 °C / Inert atmosphere 2.1: methanol / 0.75 h / 22 °C View Scheme

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

: 22795-97-7
(R)-2-aminomethyl-1-ethylpyrrolidine

: (R)-(+)-4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide

Conditions

Conditions	Yield
With 4-methyl-morpholine; chloroformic acid ethyl ester In acetone at -10 - 20℃; Temperature; Reagent/catalyst; Inert atmosphere;	7 g
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In acetone at -9℃; for 1h; Stage #2: (R)-2-aminomethyl-1-ethylpyrrolidine In acetone for 16h; Temperature;
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In acetone at -10℃; for 1h; Stage #2: (R)-2-aminomethyl-1-ethylpyrrolidine In tert-butyl methyl ether; ethyl acetate; acetone for 2h;
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In acetone at -9℃; for 1h; Stage #2: (R)-2-aminomethyl-1-ethylpyrrolidine In acetone for 16h;

4-Amino-5-ethylsulfonyl-2-methoxybenzoic acid Specification

The 4-Amino-5-ethylsulfonyl-2-methoxybenzoic acid is an organic compound with the formula C₁₀H₁₃NO₅S. The IUPAC name of this chemical is 4-amino-5-ethylsulfonyl-2-methoxybenzoic acid. With the CAS registry number 71675-87-1, it is also named as benzoic acid, 4-amino-5-(ethylsulfonyl)-2-methoxy-. The product's categories are Organic Acids; API Intermediates; Aromatics Compounds; Amines; Aromatics; Sulfur & Selenium Compounds. Besides, it is a slightly pink solid.

Physical properties about 4-Amino-5-ethylsulfonyl-2-methoxybenzoic acid are: (1)ACD/LogP: 1.57; (2)ACD/LogD (pH 5.5): 0.15; (3)ACD/LogD (pH 7.4): -1.35; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 6.51; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 6; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 5; (11)Polar Surface Area: 81.29 Å²; (12)Index of Refraction: 1.568; (13)Molar Refractivity: 61.08 cm³; (14)Molar Volume: 186.5 cm³; (15)Polarizability: 24.21×10^-24cm³; (16)Surface Tension: 56 dyne/cm; (17)Density: 1.39 g/cm³; (18)Flash Point: 274.1 °C; (19)Enthalpy of Vaporization: 84.71 kJ/mol; (20)Boiling Point: 529.6 °C at 760 mmHg; (21)Vapour Pressure: 4.78E-12 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=S(=O)(c1c(cc(OC)c(C(=O)O)c1)N)CC
(2)InChI: InChI=1/C10H13NO5S/c1-3-17(14,15)9-4-6(10(12)13)8(16-2)5-7(9)11/h4-5H,3,11H2,1-2H3,(H,12,13)
(3)InChIKey: OJVNCXHGGYYOPH-UHFFFAOYAY
(4)Std. InChI: InChI=1S/C10H13NO5S/c1-3-17(14,15)9-4-6(10(12)13)8(16-2)5-7(9)11/h4-5H,3,11H2,1-2H3,(H,12,13)
(5)Std. InChIKey: OJVNCXHGGYYOPH-UHFFFAOYSA-N

Product Name

4-Amino-5-ethylsulfonyl-2-methoxybenzoic acid

Synthetic route

4-Amino-5-ethylsulfonyl-2-methoxybenzoic acid Specification

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