Benzoic Acid → HCID 23128118, compound

HRID 358706Notes

Reaction equation

HRID 358706 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([C:21](=[O:24])[CH2:22]Cl)=[C:15]([CH:20]=1)[N:16]([CH3:19])[CH:17]=[O:18]>C(N(CC)CC)C.ClCCl>[C:1]([O:9][CH2:22][C:21]([C:14]1[CH:13]=[CH:12][C:11]([Cl:10])=[CH:20][C:15]=1[N:16]([CH3:19])[CH:17]=[O:18])=[O:24])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 243Benzoic AcidHCID 23128088HCID 23128088, compound

Product 1

HCID 23128118HCID 23128118, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of benzoic acid (18.8 g) in triethylamine (28.5 ml) and dichloromethane (110 ml) at 0° was added dropwise over 1 hour to the solution of 5'-chloro-2'-(2-chloroacetyl)-N-methylformanilide at 0° under nitrogen. The mixture was stirred for a further hour whilst maintaining the temperature at 0 to 5° and then heated under reflux overnight. After cooling, the reaction mixture was washed with water (2×100 ml), dried over magnesium sulphate, and the solvent removed by distillation to give the novel compound 2-[4-chloro-2-(N-methylformamido)phenyl]-2-oxoethyl benzoate in the form of a gum.

Workup

  1. temperaturewhilst maintaining the temperature at 0 to 5°
  2. temperatureheated
  3. temperatureunder reflux overnight
  4. temperatureAfter cooling
  5. washthe reaction mixture was washed with water (2×100 ml)
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent removed by distillation

Sources & evidence

ORD record
ord-a348ac62ed7c433f87500a34eccd6bbd
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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