Product Name

  • Name

    Ethyl 2-(3-Cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate

  • EINECS 1308068-626-2
  • CAS No. 161798-02-3
  • Article Data9
  • CAS DataBase
  • Density 1.38
  • Solubility
  • Melting Point
  • Formula C14H12N2O3S
  • Boiling Point 475.3±55.0 °C(Predicted)
  • Molecular Weight 288.327
  • Flash Point
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 161798-02-3 (Ethyl 2-(3-Cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate)
  • Hazard Symbols
  • Synonyms 2-(3-Cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylicacid ethyl ester;
  • PSA 111.19000
  • LogP 1.58198

Synthetic route

ethyl 2‐(3‐formyl‐4‐hydroxyphenyl)‐4‐methylthiazole‐5‐carboxylate
161798-01-2

ethyl 2‐(3‐formyl‐4‐hydroxyphenyl)‐4‐methylthiazole‐5‐carboxylate

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate
161798-02-3

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate

Conditions
ConditionsYield
Stage #1: ethyl 2‐(3‐formyl‐4‐hydroxyphenyl)‐4‐methylthiazole‐5‐carboxylate With hydroxylamine hydrochloride In N,N-dimethyl-formamide for 0.5h;
Stage #2: With acetyl chloride In N,N-dimethyl-formamide at 90℃;		99%
Stage #1: ethyl 2‐(3‐formyl‐4‐hydroxyphenyl)‐4‐methylthiazole‐5‐carboxylate With hydroxylamine hydrochloride In N,N-dimethyl-formamide for 0.5h;
Stage #2: With acetyl chloride In N,N-dimethyl-formamide at 90℃;		99%
With formic acid; hydroxylamine hydrochloride; sodium acetate at 100 - 105℃; for 10h;97.6%
ethyl 2-[4-(benzyloxy)-3-cyanophenyl]-4-methyl-1,3-thiazole-5-carboxylate
934470-15-2

ethyl 2-[4-(benzyloxy)-3-cyanophenyl]-4-methyl-1,3-thiazole-5-carboxylate

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate
161798-02-3

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate

Conditions
ConditionsYield
palladium-carbon In tetrahydrofuran; ethanol
With hydrogen; palladium on activated charcoal In tetrahydrofuran; ethanol at 20℃;
ethyl 2-chloro-3-oxo-butyrate
609-15-4

ethyl 2-chloro-3-oxo-butyrate

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate
161798-02-3

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: spirit / 2.5 h / 60 - 65 °C
2: methanesulfonic acid / 10 h / 75 °C
3: hydroxylamine hydrochloride; sodium formate; formic acid / 8 h / 100 °C
View Scheme
Multi-step reaction with 3 steps
1: ethanol / Reflux
2: phosphorus pentoxide
3: hydroxylamine hydrochloride; sodium acetate; formic acid
View Scheme
(2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester)
161797-99-5

(2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester)

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate
161798-02-3

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanesulfonic acid / 10 h / 75 °C
2: hydroxylamine hydrochloride; sodium formate; formic acid / 8 h / 100 °C
View Scheme
Multi-step reaction with 2 steps
1: phosphorus pentoxide
2: hydroxylamine hydrochloride; sodium acetate; formic acid
View Scheme
4-hydroxythiobenzamide
25984-63-8

4-hydroxythiobenzamide

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate
161798-02-3

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: spirit / 2.5 h / 60 - 65 °C
2: methanesulfonic acid / 10 h / 75 °C
3: hydroxylamine hydrochloride; sodium formate; formic acid / 8 h / 100 °C
View Scheme
Multi-step reaction with 3 steps
1: ethanol / Reflux
2: phosphorus pentoxide
3: hydroxylamine hydrochloride; sodium acetate; formic acid
View Scheme
C19H18N2O5S

C19H18N2O5S

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate
161798-02-3

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate

Conditions
ConditionsYield
With hydrogen
4-(benzyloxy)-3-cyanobenzenecarbothioamide
934470-14-1

4-(benzyloxy)-3-cyanobenzenecarbothioamide

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate
161798-02-3

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol / 75 °C
2: hydrogen / palladium on activated charcoal / tetrahydrofuran; ethanol / 20 °C
View Scheme
4-benzyloxyisophthalonitrile
206533-18-8

4-benzyloxyisophthalonitrile

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate
161798-02-3

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / 1,4-dioxane; N,N-dimethyl-formamide / 60 °C
2: ethanol / 75 °C
3: hydrogen / palladium on activated charcoal / tetrahydrofuran; ethanol / 20 °C
View Scheme
C14H14N2O3S

C14H14N2O3S

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate
161798-02-3

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate

Conditions
ConditionsYield
With sodium chlorite In ethanol for 2h; Inert atmosphere; Green chemistry;0.69 g
Isobutyl bromide
78-77-3

Isobutyl bromide

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate
161798-02-3

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester
160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In ethyl acetate at 65 - 70℃; for 5h; Temperature; Solvent; Reagent/catalyst;98.2%
With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 8h;92.9%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 90℃; for 3h;88%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 90℃; for 3h;88%
With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 15h;2.28 g
3-bromo-2-methyl propan-1-ol
40145-08-2

3-bromo-2-methyl propan-1-ol

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate
161798-02-3

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate

ethyl 2-[3-cyano-4-(3-hydroxy-2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylate

ethyl 2-[3-cyano-4-(3-hydroxy-2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylate

Conditions
ConditionsYield
Stage #1: ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 0.5h;
Stage #2: 3-bromo-2-methyl propan-1-ol In N,N-dimethyl-formamide at 80℃; for 4h;		63%
2-methyl-1,2-epoxypropane
558-30-5

2-methyl-1,2-epoxypropane

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate
161798-02-3

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate

ethyl 2-[3-cyano-4-(2-hydroxy-2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylate

ethyl 2-[3-cyano-4-(2-hydroxy-2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylate

Conditions
ConditionsYield
With sodium dihydrogenphosphate; potassium carbonate In water; acetonitrile at 150℃; for 12h; Sealed tube;48%
ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate
161798-02-3

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate

febuxostat

febuxostat

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 3 h / 90 °C
2: sodium hydroxide; water / methanol / 1 h / 45 - 60 °C
View Scheme
ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate
161798-02-3

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate

2-[3-cyano-4-(3-hydroxy-2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylic acid

2-[3-cyano-4-(3-hydroxy-2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.5 h / 80 °C
1.2: 4 h / 80 °C
2.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 1.5 h / 60 °C
View Scheme
ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate
161798-02-3

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate

2-[3-cyano-4-(2-hydroxy-2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylic acid

2-[3-cyano-4-(2-hydroxy-2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate; sodium dihydrogenphosphate / water; acetonitrile / 12 h / 150 °C / Sealed tube
2: sodium hydroxide; water / ethanol; tetrahydrofuran / 1.5 h / 60 °C
View Scheme
ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate
161798-02-3

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate

3-{2-cyano-4-[5-(ethoxycarbonyl)-4-methylthiazol-2-yl]phenoxy}-2-methylpropanoic acid

3-{2-cyano-4-[5-(ethoxycarbonyl)-4-methylthiazol-2-yl]phenoxy}-2-methylpropanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.5 h / 80 °C
1.2: 4 h / 80 °C
2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite; sodium chlorite / water; acetonitrile; aq. phosphate buffer / 6 h / 35 °C / pH 6.7
View Scheme
ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate
161798-02-3

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate

2-[4-(2-carboxypropoxy)-3-cyanophenyl]-4-methylthiazole-5-carboxylic acid

2-[4-(2-carboxypropoxy)-3-cyanophenyl]-4-methylthiazole-5-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 0.5 h / 80 °C
1.2: 4 h / 80 °C
2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite; sodium chlorite / water; acetonitrile; aq. phosphate buffer / 6 h / 35 °C / pH 6.7
3.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 1.5 h / 60 °C
View Scheme
ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate
161798-02-3

ethyl-2-(3-cyano-4-hydroxy phenyl)-4-methyl thiozole-5-carboxylate

methyl 2-(bromomethyl)propenoate
4224-69-5

methyl 2-(bromomethyl)propenoate

C19H18N2O5S

C19H18N2O5S

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 80℃;

Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate Specification

The systematic name of Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate is (2E)-2-(3-cyano-4-oxocyclohexa-2,5-dien-1-ylidene)-4-methyl-2,3-dihydro-1,3-thiazole-5-carboxylic acid. With the CAS registry number 161798-02-3, it is also named as 2-(3-Cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylicacid ethyl ester. The product's category is Pharmaceutical Intermediates. In addition, its molecular formula is C14H12N2O3S and molecular weight is 288.32.

The other characteristics of Ethyl 2-(3-cyano-4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate can be summarized as: (1)#H bond acceptors: 5; (2)#H bond donors: 2; (3)#Freely Rotating Bonds: 1; (4)Polar Surface Area: 115.49Å2; (5)Index of Refraction: 1.701; (6)Molar Refractivity: 65.399 cm3; (7)Molar Volume: 168.979 cm3; (8)Polarizability: 25.926x10-24cm3; (9)Surface Tension: 77.144 dyne/cm; (10)Enthalpy of Vaporization: 67.433 kJ/mol.

People can use the following data to convert to the molecule structure.
(1)SMILES: O=C/2C(\C#N)=C/C(=C1/S\C(=C(/N1)C)C(=O)O)\C=C\2
(2)InChI: InChI=1/C12H8N2O3S/c1-6-10(12(16)17)18-11(14-6)7-2-3-9(15)8(4-7)5-13/h2-4,14H,1H3,(H,16,17)/b11-7+
(3)InChIKey: YETZYXMCWPWBML-YRNVUSSQBT
(4)Std. InChI: InChI=1S/C12H8N2O3S/c1-6-10(12(16)17)18-11(14-6)7-2-3-9(15)8(4-7)5-13/h2-4,14H,1H3,(H,16,17)/b11-7+
(5)Std. InChIKey: YETZYXMCWPWBML-YRNVUSSQSA-N

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