Benzoic Acid → HCID 23128169, compound

HRID 358710Notes

Reaction equation

HRID 358710 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[CH2:18][C:19]([C:21]1[CH:30]=[C:29]([F:31])[C:28]([F:32])=[CH:27][C:22]=1[N:23]([CH3:26])[CH:24]=[O:25])=[O:20]>ClCCl>[C:1]([O:9][CH2:18][C:19]([C:21]1[CH:30]=[C:29]([F:31])[C:28]([F:32])=[CH:27][C:22]=1[N:23]([CH3:26])[CH:24]=[O:25])=[O:20])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 8471TriethylamineHCID 23128138HCID 23128138, compound

Product 1

HCID 23128169HCID 23128169, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzoic acid (40.3 g) and triethylamine (61 ml) in dichloromethane (200 ml) was added dropwise over 20 minutes to the solution of 2'-(2-chloroacetyl)-4',5'-difluoro-N-methylformanilide at 0° under nitrogen and the resultant solution stirred overnight at ambient temperature. The mixture was washed with water (3×250 ml) and the solvent removed by distillation. The residue was purified by flash chromatography on a silica gel eluted with dichloromethane:methanol (50:1) to give the novel compound 2-[4,5-difluoro-2-(N-methylformamido)phenyl-2-oxoethyl benzoate in the form of an oil.

Workup

  1. washThe mixture was washed with water (3×250 ml)
  2. customthe solvent removed by distillation
  3. customThe residue was purified by flash chromatography on a silica gel
  4. washeluted with dichloromethane:methanol (50:1)

Sources & evidence

ORD record
ord-3153ca9017b14629bc10abd4a70eda5f
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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