Formic Acid → N-(2-Benzoyl-4-chlorophenyl)formamide

HRID 2082689Notes

Reaction equation

HRID 2082689 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[CH:17](O)=[O:18]>>[Cl:16][C:13]1[CH:14]=[CH:15][C:2]([NH:1][CH:17]=[O:18])=[C:3]([CH:12]=1)[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:5]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 128702-Amino-5-chlorobenzophenone

Product 1

HCID 82576N-(2-Benzoyl-4-chlorophenyl)formamideYield 98%

Procedure

A solution of 34.7 parts of 2-amino-5-chlorobenzophenone in 100 volume parts of formic acid is refluxed for 1.5 hour, and the excess formic acid is distilled off under reduced pressure. The residue is dissolved in 30 volume parts of ethyl acetate, and washed with a saturated aqueous solution of sodium bicarbonate and water in this order, and dried over sodium sulfate, followed by distilling off the solvent. Treatment of the residue with n-hexane gives 5-chloro-2-formamidobenzophenone as pale yellow crystals. Recrystallization of the crystals from ethanol gives pale yellow granules melting at 92.5° to 93° C. Yield: 98%

Workup

  1. distillationthe excess formic acid is distilled off under reduced pressure
  2. dissolutionThe residue is dissolved in 30 volume parts of ethyl acetate
  3. washwashed with a saturated aqueous solution of sodium bicarbonate and water in this order
  4. dry with materialdried over sodium sulfate
  5. distillationby distilling off the solvent

Sources & evidence

ORD record
ord-33ee87042a3a4b6fbc8a49a817382069
Source dataset
uspto-grants-1978_04
Patent number
US04082764

Reaction notes

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