4-Fluorobenzoyl chloride → N-Methylbenzamide

HRID 981516

Reaction equation

HRID 981516 reaction equation
FC1C=CC(CNC)=CC=1.F[C:12]1[CH:21]=[CH:20][C:15]([C:16]([NH:18][CH3:19])=[O:17])=[CH:14][CH:13]=1.FC1C=CC(C(Cl)=O)=CC=1>CN>[CH3:19][NH:18][C:16](=[O:17])[C:15]1[CH:20]=[CH:21][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 7368601-(4-fluorophenyl)-N-methylmethanamineHCID 40742474-fluoro-N-methylbenzamide

Product 1

HCID 11954N-Methylbenzamide

Reagents, catalysts & solvents 1

HCID 6329MethylamineSolvent

Procedure

This compound was prepared from 4-Fluoro-N-methylbenzylamine which in turn was prepared from 4-Fluoro-N-methylbenzamide. Practical details are as follows: 4-Fluorobenzoyl chloride (25g) was added dropwise to a stirred aqueous solution of methylamine (40% w/v; 250 ml) at 0° C. over 30 min. The mixture was stirred for 12 h at room temperature, concentrated to half volume and the resulting crystalline precipitate was collected and recrystallized from water to furnish the N-methylbenzamide as colourless needles, (24.1 g; 89.1%), m.p. 131°-132° C.

Workup

  1. concentrationconcentrated to half volume
  2. customthe resulting crystalline precipitate was collected
  3. customrecrystallized from water

Sources & evidence

ORD record
ord-afdb13066def4d9cbbc7a209980b998e
Source dataset
uspto-grants-1991_02
Patent number
US04992444

Linked notes

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