Dimethylformamide → N-acetyl-2-(triphenylmethylthio)acetamide

HRID 1855764Notes

Reaction equation

HRID 1855764 reaction equation
[C:1]1([C:7]([SH:20])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)C=O.C(N(CC)CC)C.[C:33]([NH:36][C:37](=[O:40])[CH2:38]Cl)(=[O:35])[CH3:34]>O>[C:33]([NH:36][C:37](=[O:40])[CH2:38][S:20][C:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:35])[CH3:34]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 77281Benzenemethanethiol, alpha,alpha-diphenyl-HCID 2366697N-acetyl-2-chloroacetamide

Product 1

HCID 12837901N-acetyl-2-(triphenylmethylthio)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 100.4 g. (0.40 mole) of triphenylmethylmercaptan in 500 ml. of dry dimethylformamide was added 40.4 g. (0.40 mole) of dry triethylamine. The reaction mixture was cooled in ice and stirred as portions of 54.2 g. (0.40 mole) of the product of Step A above were added over 10 minutes. The reaction mixture was stirred an additional hour with ice cooling and then overnight at room temperature. Water was then added carefully to the reaction mixture until just before the cloud point, when the mixture was seeded and crystallization began. Yield of product was 98.5 g. with an m.p. of 147°-149° C.

Workup

  1. additionTo a suspension of 100.4 g
  2. temperatureThe reaction mixture was cooled in ice
  3. stirringThe reaction mixture was stirred an additional hour with ice cooling
  4. customovernight
  5. customat room temperature
  6. customcrystallization

Sources & evidence

ORD record
ord-b0d4c296063341559b42c4233f814a52
Source dataset
uspto-grants-1980_08
Patent number
US04216160

Reaction notes

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