Benzoic Acid → HCID 86744647, compound

HRID 358685Notes

Reaction equation

HRID 358685 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]([CH3:31])=[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]([CH3:31])=[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 8471TriethylamineHCID 23128093HCID 23128093, compound

Product 1

HCID 86744647HCID 86744647, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzoic acid (30.3 g) and triethylamine (50.1 ml) in dichloromethane (150 ml) was added dropwise at 0° over a period of 15 minutes to the solution of 2'-(2-chloroacetyl)-5'-methyl-N-methylformanilide obtained above. The resultant solution was allowed to warm to ambient temperature and then heated under reflux overnight. After cooling the reaction mixture was washed with water (2×200 ml), dried over magnesium sulphate and evaporated to give crude 2-[4-methyl-2-(N-methylformamido)phenyl]-2-oxoethyl benzoate.

Workup

  1. customobtained above
  2. temperatureheated
  3. temperatureunder reflux overnight
  4. temperatureAfter cooling the reaction mixture
  5. washwas washed with water (2×200 ml)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-d8a326d10cf844c388ac5f238f24c482
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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