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

HRID 1374837Notes

Reaction equation

HRID 1374837 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[C:6]1([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1(C)C=CC=CC=1.O1CCCC1>[Cl:1][CH2:2][C:3]([N:12]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4]

Participants

5

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 11487Diphenylamine

Product 1

HCID 2244812-chloro-N,N-diphenyl-AcetamideYield 75.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

Chloroacetyl chloride (0.32 ml, 4.02 mmol) was dissolved in a mixed solvent of toluene (6 ml) and tetrahydrofuran (2 ml). The solution was added with diphenylamine (690 mg, 4.08 mmol) at room temperature, and the heated at 100° C. for 80 minutes. The solvent was evaporated under reduced pressure, and the solid precipitated was suspended and washed in ethyl ether. The solid was collected by filtration and dried under reduced pressure to obtain the title compound as colorless solid (746 mg, yield: 75%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe solid precipitated
  3. washwashed in ethyl ether
  4. filtrationThe solid was collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-f223e951be944d738507469f0bceee6f
Source dataset
uspto-grants-2007_01
Patent number
US07166617B2

Reaction notes

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