Benzoic Acid → 2-[2-(N-methylformamido)phenyl]-2-oxoethyl benzoate

HRID 358661Notes

Reaction equation

HRID 358661 reaction equation
C(N(CC)CC)C.[C:8]([OH:16])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl[CH2:18][C:19]([C:21]1[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=1[N:23]([CH3:26])[CH:24]=[O:25])=[O:20]>ClCCl>[C:8]([O:16][CH2:18][C:19]([C:21]1[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=1[N:23]([CH3:26])[CH:24]=[O:25])=[O:20])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 8471TriethylamineHCID 23128087N-[2-(Chloroacetyl)phenyl]-N-methylformamide

Product 1

HCID 867446442-[2-(N-methylformamido)phenyl]-2-oxoethyl benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (362.8 ml) was added to a stirred mixture of benzoic acid (239.1 g) and dichloromethane (1120 ml) at 0° and the resultant solution was added dropwise over a period of 1 hour to the solution of 2'-(2-chloroacetyl)-N-methylformanilide under nitrogen whilst maintaining the temperature below 5°. The resulting solution was stirred overnight at ambient temperature, washed with water (2×1250 ml), dried over magnesium sulphate and the solvent removed by distillation at 50° to give a solid residue. Trituration with petroleum ether (b.p. 60°-80°, 1 1) gave the novel compound 2-[2-(N-methylformamido)phenyl]-2-oxoethyl benzoate, m.p. 100°-102°.

Workup

  1. temperaturewhilst maintaining the temperature below 5°
  2. washwashed with water (2×1250 ml)
  3. dry with materialdried over magnesium sulphate
  4. customthe solvent removed by distillation at 50°
  5. customto give a solid residue

Sources & evidence

ORD record
ord-69e8ecb96b6842bcbeb21f5b436cfd00
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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