Chloroacetyl chloride → 2-chloro-N,N-diphenyl-Acetamide

HRID 751323

Reaction equation

HRID 751323 reaction equation
[C:1]1([NH:7][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.[Cl:21][CH2:22][C:23](Cl)=[O:24]>C1(C)C=CC=CC=1>[C:8]1([N:7]2[C:1]3[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:22][C:23]2=[O:24])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1.[Cl:21][CH2:22][C:23]([N:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:24]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 11487Diphenylamine

Product 2

HCID 2244812-chloro-N,N-diphenyl-AcetamideYield 83.8%HCID 3147871-Phenyloxindole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Conditions

Temperature
60 °C

Procedure

The title compound is prepared in accordance with the procedures described in Latrell, Bartmann, Granzier DE 2 707 268 (1978) as follows. A solution of diphenylamine (40 g, 237 mmol) and triethylamine (66.1 mL, 474 mmol) in toluene (65 mL) is added dropwise to a solution of chloroacetyl chloride (20.7 mL, 260 mmol) in toluene (40 mL) while cooling in an ice-water bath. The cold bath is removed and the reaction mixture is heated at 55-65° C. for 3 hr. The cooled reaction mixture is diluted with toluene (100 mL), filtered and the filtrate concentrated to give 2-chloro-N,N-diphenylacetamide (24.4 g, 42% yield) as a light brown solid. NMR (CDCl3) 7.56-7.19 (10H, m), 4.01 (2H, s).

Workup

  1. temperaturewhile cooling in an ice-water bath
  2. customThe cold bath is removed
  3. customThe cooled reaction mixture
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-44ae802aadf344cbb7d0782b65822a65
Source dataset
uspto-grants-2008_07
Patent number
US07405300B2

Linked notes

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