Benzoic Acid → 2-[4-fluoro-2-(N-methylformamido)phenyl]-2-oxoethyl benzoate

HRID 358665Notes

Reaction equation

HRID 358665 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]=[CH:29][C:28]([F:31])=[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]=[CH:29][C:28]([F:31])=[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 8471Triethylamine2×HCID 23128132N-[2-(Chloroacetyl)-5-fluorophenyl]-N-methylformamide

Product 1

HCID 867446452-[4-fluoro-2-(N-methylformamido)phenyl]-2-oxoethyl benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Benzoic acid (42.7 g) and triethylamine (64.8 ml) were dissolved in dichloromethane (250 ml) at 0° and this solution was added to the dichloromethane solution of 2'-(2-chloroacetyl)-5'-fluoro-N-methylformanilide over a period of hour whilst maintaining the temperature below 5° with ice/water bath cooling. After stirring for 1 hour at 5°, the mixture was heated under reflux under nitrogen for 16 hours. Further triethylamine (16 ml) was added and the mixture heated under reflux for a further 16 hours. The mixture was allowed to cool to ambient temperature, washed with water (2×250 ml) and dried over magnesium sulphate. Evaporation of the solvent gave the novel compound 2-[4-fluoro-2-(N-methylformamido)phenyl]-2-oxoethyl benzoate, m.p. 93°-95°.

Workup

  1. temperaturewhilst maintaining the temperature below 5° with ice/water bath
  2. temperaturecooling
  3. temperaturethe mixture was heated
  4. temperatureunder reflux under nitrogen for 16 hours
  5. temperaturethe mixture heated
  6. temperatureunder reflux for a further 16 hours
  7. washwashed with water (2×250 ml)
  8. dry with materialdried over magnesium sulphate
  9. customEvaporation of the solvent

Sources & evidence

ORD record
ord-44058c9dfbaa4e5b9f7b5a7f0280576f
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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