• Name

  2-[(Diphenylmethyl)thio]acetamide

• EINECS 614-564-6
• CAS No. 68524-30-1
• Article Data21
• CAS DataBase
• Density 1.184 g/cm³
• Solubility
• Melting Point 109-110 °C(Solv: methanol (67-56-1); water (7732-18-5))
• Formula C₁₅H₁₅NOS
• Boiling Point 427.707 °C at 760 mmHg
• Molecular Weight 257.356
• Flash Point 212.47 °C
• Transport Information
• Appearance White crystalline powder
• Safety 60-61
• Risk Codes 22-50/53
• Molecular Structure
• Hazard Symbols Xn,N
• Synonyms 2-(Benzhydrylthio)acetamide;
• PSA 68.39000
• LogP 3.69480

Synthetic route

90-99-3

diphenylchloromethane

79-07-2

Chloroacetamide

68524-30-1

2-(diphenylmethylthio)acetamide

Conditions

Conditions	Yield
Stage #1: diphenylchloromethane With thiourea; potassium iodide In water at 70 - 75℃; for 1.5h; Stage #2: With sodium hydroxide In water at 15 - 24℃; Stage #3: Chloroacetamide With triethylamine more than 3 stages;	97.9%
Stage #1: diphenylchloromethane With thiourea In isopropyl alcohol at 100℃; for 2h; Sealed tube; Stage #2: Chloroacetamide With potassium hydroxide In methanol; isopropyl alcohol at 60℃; for 2h; Sonication;

68524-29-8

benzhydrylsulfanyl acetyl chloride

68524-30-1

2-(diphenylmethylthio)acetamide

Conditions

Conditions	Yield
With ammonium hydroxide In tetrahydrofuran; dichloromethane at 0℃; for 1h;	96%
With ammonium hydroxide In dichloromethane for 2h;	17.0 g
With ammonium hydroxide In dichloromethane at 2℃; for 20h;
With ammonium hydroxide In dichloromethane; water at 0℃; for 1h;	14.39 g
With ammonium hydroxide In water at 0 - 20℃; for 20h; Alkaline conditions;

91-01-0

1,1-Diphenylmethanol

18877-99-1

sodium S-(carbamoylmethyl)thiosulfate

68524-30-1

2-(diphenylmethylthio)acetamide

Conditions

Conditions	Yield
With formic acid In water at 60℃; for 0.333333h;	92%

63547-22-8

(benzhydrylthio)acetic acid

68524-30-1

2-(diphenylmethylthio)acetamide

Conditions

Conditions	Yield
With ammonium carbamate; novozyme-435 In tert-butyl alcohol at 60℃; for 168h;	90%
Stage #1: (benzhydrylthio)acetic acid With thionyl chloride In benzene for 2h; Reflux; Stage #2: With ammonia In dichloromethane at 20℃; for 2h; Cooling with ice;	69%
Stage #1: (benzhydrylthio)acetic acid With thionyl chloride In benzene at 20℃; for 1h; Inert atmosphere; Reflux; Stage #2: With ammonium hydroxide In dichloromethane at 0℃; for 1h;	54%

683-57-8

bromo-acetic acid amide

90280-15-2

diphenylmethylisothiouronium bromide

68524-30-1

2-(diphenylmethylthio)acetamide

Conditions

Conditions	Yield
Stage #1: diphenylmethylisothiouronium bromide With sodium hydroxide In water at 40 - 80℃; Stage #2: bromo-acetic acid amide at 60 - 70℃; for 5 - 6h;	90%

90280-15-2

diphenylmethylisothiouronium bromide

79-07-2

Chloroacetamide

68524-30-1

2-(diphenylmethylthio)acetamide

Conditions

Conditions	Yield
Stage #1: diphenylmethylisothiouronium bromide With sodium hydroxide In water at 40 - 85℃; Stage #2: Chloroacetamide at 30 - 70℃; for 5 - 6h;	88%
Stage #1: diphenylmethylisothiouronium bromide With sodium hydroxide In methanol; water at 40 - 60℃; for 0.5h; Stage #2: Chloroacetamide for 3.16667 - 4.16667h; Heating / reflux;	71%

758-08-7

Thioglycolamide

91-01-0

1,1-Diphenylmethanol

68524-30-1

2-(diphenylmethylthio)acetamide

Conditions

Conditions	Yield
With Nafion-H In 2-methyltetrahydrofuran at 20℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Green chemistry;	88%
With trifluoroacetic acid at 20℃; for 4h;	17%
With ammonia; trifluoroacetic acid In methanol at 20℃; for 4h;	17%

(+)-Modafinil

68524-30-1

2-(diphenylmethylthio)acetamide

Conditions

Conditions	Yield
With acetyl chloride; potassium iodide In acetic acid at 20℃; for 0.5h;	87%

121-44-8

triethylamine

90-99-3

diphenylchloromethane

79-07-2

Chloroacetamide

68524-30-1

2-(diphenylmethylthio)acetamide

Conditions

Conditions	Yield
Stage #1: diphenylchloromethane With thiourea; potassium iodide In water at 70 - 95℃; for 2h; Stage #2: With sodium hydroxide In water at 15 - 24℃; Stage #3: triethylamine; Chloroacetamide more than 3 stages;	81.4%

...Expand

63547-26-2

2-benzhydrylsulfanylacetonitrile

68524-30-1

2-(diphenylmethylthio)acetamide

Conditions

Conditions	Yield
With potassium hydroxide In ethanol for 6h; Reflux;	75%

63547-23-9

(diphenylmethyl)(ethyl acetate)sulfide

68524-30-1

2-(diphenylmethylthio)acetamide

Conditions

Conditions	Yield
With ammonia at 100℃;

91-01-0

1,1-Diphenylmethanol

BF3(C2H5)2O

BF3(C2H5)2O

68524-30-1

2-(diphenylmethylthio)acetamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 99.9 percent / SOCl2 / benzene / 1 h / Heating 2: 96 percent / NH4OH / CH2Cl2; tetrahydrofuran / 1 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: 90 percent / ammonium carbamate; Novozyme-435 / 2-methyl-propan-2-ol / 168 h / 60 °C View Scheme
Multi-step reaction with 3 steps 1: 99 percent / trifluoroacetic acid / 3 h / 20 °C 2: thionyl chloride / benzene / 1.5 h / Heating 3: 17.0 g / aq. NH4OH / CH2Cl2 / 2 h View Scheme

91-01-0

1,1-Diphenylmethanol

68524-30-1

2-(diphenylmethylthio)acetamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: concentrated aqueous HCl 2: concentrated sulfuric acid 3: ethanolic NH3 / 100 °C View Scheme
Multi-step reaction with 3 steps 1: trifluoroacetic acid / 20 °C 2: potassium carbonate / acetone / 4 h / Reflux 3: ammonium hydroxide; ammonium chloride / methanol / 72 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1: Lawessons reagent / toluene / 3 h / Reflux; Inert atmosphere 2: potassium carbonate / acetone / 6 h 3: potassium hydroxide / ethanol / 6 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: trifluoroacetic acid / 3 h 2: thionyl chloride / benzene / 2 h / Reflux 3: ammonium hydroxide / dichloromethane / 20 h / 2 °C View Scheme
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid / 3 h / 20 °C 2.1: thionyl chloride / benzene / 2 h / Reflux 2.2: 2 h / 20 °C / Cooling with ice View Scheme

4237-48-3

diphenylmethanethiol

79-07-2

Chloroacetamide

68524-30-1

2-(diphenylmethylthio)acetamide

Conditions

Conditions	Yield
In tetrahydrofuran; water at 70℃; for 1.25h;
In water; chlorobenzene at 70℃; for 0.75h;

118286-24-1

methyl diphenylmethylmercaptoacetate

68524-30-1

2-(diphenylmethylthio)acetamide

Conditions

Conditions	Yield
With ammonia In methanol at 15℃; for 1h;
With ammonium hydroxide; ammonium chloride In methanol at 50℃; for 72h;

ammonium carbamate

NH4OH-THF

NH4OH-THF

63547-22-8

(benzhydrylthio)acetic acid

68524-29-8

benzhydrylsulfanyl acetyl chloride

68524-30-1

2-(diphenylmethylthio)acetamide

Conditions

Conditions	Yield
With thionyl chloride In dichloromethane; water; tert-butyl alcohol; benzene

...Expand

Reaxys ID: 19820829

Reaxys ID: 19820829

Reaxys ID: 19820830

Reaxys ID: 19820830

68524-30-1

2-(diphenylmethylthio)acetamide

4237-48-3

diphenylmethanethiol

68524-30-1

2-(diphenylmethylthio)acetamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 6 h 2: potassium hydroxide / ethanol / 6 h / Reflux View Scheme

776-74-9

Bromodiphenylmethane

68524-30-1

2-(diphenylmethylthio)acetamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: water; acetone / 3 h / 20 - 70 °C / Inert atmosphere 2: thionyl chloride / benzene / 1 h / Inert atmosphere; Reflux 3: ammonium hydroxide / water; dichloromethane / 1 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1.1: water; acetone / 3 h / 20 - 70 °C / Inert atmosphere 2.1: thionyl chloride / benzene / 1 h / 20 °C / Inert atmosphere; Reflux 2.2: 1 h / 0 °C View Scheme

68524-30-1

2-(diphenylmethylthio)acetamide

112111-43-0, 112111-47-4, 112111-49-6, 68693-11-8

Modafinil

Conditions

Conditions	Yield
With phthaloyl peroxide In dichloromethane at 25℃; for 8h; Schlenk technique; chemoselective reaction;	99%
With 1-methyl-3,5-dinitropyridinium trifluoromethanesulfonate; dihydrogen peroxide In methanol; water at 25℃; for 21.5h; Reagent/catalyst;	98%
With 1-octyl-3,5-dinitropyridinium triflate; dihydrogen peroxide In aq. phosphate buffer; chloroform at 25℃; for 4h; pH=2; Reagent/catalyst; Green chemistry; chemoselective reaction;	98%

68524-30-1

2-(diphenylmethylthio)acetamide

l-modafinil

Conditions

Conditions	Yield
Stage #1: 2-(diphenylmethylthio)acetamide; titanium(IV) isopropylate; diethyl (2R,3R)-tartrate In water; toluene at 55℃; for 0.833333h; Stage #2: With Cumene hydroperoxide; N-ethyl-N,N-diisopropylamine In water; toluene at 25℃; for 1h; Product distribution / selectivity;	98.5%
Stage #1: 2-(diphenylmethylthio)acetamide; titanium(IV) isopropylate; diethyl (2S,3S)-tartrate In water; toluene at 55℃; for 0.833333h; Stage #2: With Cumene hydroperoxide; triethylamine In water; toluene at 25℃; for 1h; Product distribution / selectivity;	90.3%
Stage #1: 2-(diphenylmethylthio)acetamide; titanium(IV) isopropylate; diethyl (2S,3S)-tartrate In toluene at 55℃; for 0.833333h; Stage #2: With Cumene hydroperoxide; N-ethyl-N,N-diisopropylamine In toluene at 25℃; for 1h; Product distribution / selectivity;	90.3%

68524-30-1

2-(diphenylmethylthio)acetamide

A

112111-43-0, 112111-47-4, 112111-49-6, 68693-11-8

Modafinil

B

Modafinil sulfone

Conditions

Conditions	Yield
With dihydrogen peroxide In acetic acid at 40℃; for 6h;	A 95.73% B 0.083%
With dihydrogen peroxide; acetic acid In methanol; water at 40 - 65℃; for 1 - 28.75h; Product distribution / selectivity;

68524-30-1

2-(diphenylmethylthio)acetamide

63547-26-2

2-benzhydrylsulfanylacetonitrile

Conditions

Conditions	Yield
With (dimethoxy)methylsilane; copper diacetate; 1,2-bis-(dicyclohexylphosphino)ethane In tetrahydrofuran at 20℃; for 12h; Sealed tube;	77%

68524-30-1

2-(diphenylmethylthio)acetamide

Modafinil sulfone

Conditions

Conditions	Yield
With ε-phthalimido-peroxy-hexanoic acid In dichloromethane at 20℃; for 6h;	72%

68524-30-1

2-(diphenylmethylthio)acetamide

2-(benzhydrylthio)ethanethioamide

Conditions

Conditions	Yield
With Lawessons reagent In 1,4-dioxane for 2h; Reflux;	62%
With tetraphosphorus decasulfide; potassium sulfide; toluene
With Lawessons reagent

68524-30-1

2-(diphenylmethylthio)acetamide

d-modafinil

l-modafinil

Conditions

Conditions	Yield
Stage #1: 2-(diphenylmethylthio)acetamide; titanium(IV) isopropylate; diethyl (2R,3R)-tartrate In dichloromethane; water at -30 - 20℃; for 0.833333h; Stage #2: With Cumene hydroperoxide In dichloromethane; water at -30 - -25℃; for 1.75h; Conversion of starting material;	A 42% B n/a
Stage #1: 2-(diphenylmethylthio)acetamide; titanium(IV) isopropylate; diethyl (2S,3S)-tartrate In water; ethyl acetate at 25 - 55℃; for 0.166667 - 0.833333h; Stage #2: With Cumene hydroperoxide; triethylamine In water; ethyl acetate at 25 - 55℃; for 0.0833333 - 1h; Product distribution / selectivity;	A n/a B n/a
Stage #1: 2-(diphenylmethylthio)acetamide; titanium(IV) isopropylate; diethyl (2S,3S)-tartrate In water; ethyl acetate at 55℃; for 0.833333h; Stage #2: With Cumene hydroperoxide In water; ethyl acetate at 25℃; for 1h; Product distribution / selectivity;	A n/a B n/a
Stage #1: 2-(diphenylmethylthio)acetamide; titanium(IV) isopropylate; diethyl (2S,3S)-tartrate In water; toluene at 55℃; for 0.833333h; Stage #2: With Cumene hydroperoxide In water; toluene at 25℃; for 1h; Product distribution / selectivity;	A n/a B n/a

68524-30-1

2-(diphenylmethylthio)acetamide

6266-48-4

2,4,6-tribenzhydrylphenol

Conditions

Conditions	Yield
With trifluoroacetyl peroxide In trifluoroacetic acid at 10℃; for 0.166667h; Mechanism;	34%

68524-30-1

2-(diphenylmethylthio)acetamide

2-(benzhydrylmercapto-methyl)-4,5-dihydro-1H-imidazole

Conditions

Conditions	Yield
With tetraphosphorus decasulfide; potassium sulfide; toluene at 100℃; Erhitzen des Reaktionsprodukts mit Aethylendiamin in Toluol;

68524-30-1

2-(diphenylmethylthio)acetamide

A

112111-43-0, 112111-47-4, 112111-49-6, 68693-11-8

Modafinil

B

63547-24-0

modafinil acid

Conditions

Conditions	Yield
Stage #1: 2-(diphenylmethylthio)acetamide With acetic acid In methanol at 30 - 40℃; for 0.25h; Stage #2: With dihydrogen peroxide In methanol; water at 38 - 43℃; for 24h; Product distribution / selectivity;

68524-30-1

2-(diphenylmethylthio)acetamide

A

112111-43-0, 112111-47-4, 112111-49-6, 68693-11-8

Modafinil

B

63547-24-0

modafinil acid

C

Modafinil sulfone

Conditions

Conditions	Yield
Stage #1: 2-(diphenylmethylthio)acetamide With acetic acid In methanol at 30 - 40℃; for 0.25h; Stage #2: With dihydrogen peroxide In methanol; water at 38 - 43℃; for 24h; Product distribution / selectivity;

...Expand

68524-30-1

2-(diphenylmethylthio)acetamide

A

112111-43-0

Nuvigil

B

(+)-Modafinil

Conditions

Conditions	Yield
With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate In tetrachloromethane at 20℃; for 48h; Title compound not separated from byproducts.;
With bis(acetylacetonate)oxovanadium; 2,4-di-tert-butyl-6-((E)-(((1R,2S)-2-hydroxy-1,2-diphenylethyl)imino)methyl)phenol; dihydrogen peroxide In chloroform at 20℃; for 3.5h; optical yield given as %ee; enantioselective reaction;
With NADP In isopropyl alcohol at 25℃; for 20h; pH=8; Catalytic behavior; Alkaline conditions; enantioselective reaction;	A n/a B n/a
With tert.-butylhydroperoxide at 20℃; Enzymatic reaction;
Stage #1: 2-(diphenylmethylthio)acetamide With iron(III) trifluoromethanesulfonate; C37H56N4O4 In tert-butyl methyl ether at 35℃; for 0.5h; Inert atmosphere; Stage #2: With dihydrogen peroxide In tert-butyl methyl ether; water at 25℃; for 8h; Inert atmosphere; Overall yield = 94 percent; Overall yield = 25.6 mg; enantioselective reaction;	A n/a B n/a

2-[(Diphenylmethyl)thio]acetamide Chemical Properties

2-[(Diphenylmethyl)thio]acetamide Specification