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

HRID 1065290Notes

Reaction equation

HRID 1065290 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.C(N(CC)CC)C.CN(C)C=O.[C:33]([NH:36][C:37](=[O:40])[CH2:38]Cl)(=[O:35])[CH3:34]>O.C1C=CC=CC=1>[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

7

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 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of 0.009 mole of triphenylmethyl mercaptan and 0.009 mole of triethylamine in 10 ml. of dimethylformamide is cooled to 0°-5° C. in an ice bath and 0.009 mole of N-acetyl-2-chloroacetamide added. The reaction mixture is stirred at ambient temperature for three hours and then poured into 100 ml. of benzene and 100 ml. of water. The organic layer is separated, washed well with water, dried over sodium sulfate and concentrated to dryness. The residue is crystallized under petroleum ether to give 2.2 g. of Nacetyl-2-(triphenylmethylthio) acetamide.

Workup

  1. additionpoured into 100 ml
  2. customThe organic layer is separated
  3. washwashed well with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue is crystallized under petroleum ether
  7. customto give 2.2 g

Sources & evidence

ORD record
ord-fc25da623359446fa5544f1cfa018c21
Source dataset
uspto-grants-1982_05
Patent number
US04329363

Reaction notes

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