Dichloroacetyl chloride → N-(2-Benzoylphenyl)-2,2-dichloroacetamide

HRID 1579525Notes

Reaction equation

HRID 1579525 reaction equation
[Cl:1][CH:2]([Cl:6])[C:3](Cl)=[O:4].[NH2:7][C:8]1[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11]>ClCCl.C(N(CC)CC)C>[C:10]([C:9]1[CH:18]=[CH:19][CH:20]=[CH:21][C:8]=1[NH:7][C:3](=[O:4])[CH:2]([Cl:6])[Cl:1])(=[O:11])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 6593Dichloroacetyl chlorideHCID 760802-Aminobenzophenone

Product 1

HCID 614210N-(2-Benzoylphenyl)-2,2-dichloroacetamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

Dichloroacetylchloride (88 ml) in dichloromethane (200 ml) was added dropwise to a stirred solution of 2-aminobenzophenone (157.6g) in dichloromethane (400 ml) and triethylamine (116 ml) while keeping the temperature between 20°-30°C by cooling in ice. On completion of the addition the reaction was stirred at room temperature for 1.5 hours. The reaction mixture was washed with successive portions of distilled water-dilute hydrochloric acid and finally distilled water. After drying over anhydrous magnesium sulphate the solvent was removed under reduced pressure to leave a solid which on recrystallisation from absolute, ethanol gave 222 g of 2'-benzoyl-2,2-dichloroacetanilide, m.p. 112°-114°C.

Workup

  1. custombetween 20°-30°C
  2. temperatureby cooling in ice
  3. additionOn completion of the addition the reaction
  4. washThe reaction mixture was washed with successive portions of distilled water-dilute hydrochloric acid and finally distilled water
  5. dry with materialAfter drying over anhydrous magnesium sulphate the solvent
  6. customwas removed under reduced pressure
  7. customto leave a solid which
  8. customon recrystallisation from absolute, ethanol

Sources & evidence

ORD record
ord-51486e70cdd94bf28601bf0223c4fa7d
Source dataset
uspto-grants-1976_01
Patent number
US03931226

Reaction notes

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