Water → N-methyl-3-(2,4-difluorophenylthio)-4-nitrobenzamide

HRID 1087177Notes

Reaction equation

HRID 1087177 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])[C:13](Cl)=[O:14].[CH3:22][NH2:23].O>CCOCC>[CH3:22][NH:23][C:13](=[O:14])[C:12]1[CH:16]=[CH:17][C:18]([N+:19]([O-:21])=[O:20])=[C:10]([S:9][C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 103592393-(2,4-Difluorophenylthio)-4-nitrobenzoyl chloride

Product 1

HCID 10471482N-methyl-3-(2,4-difluorophenylthio)-4-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 3-(2,4-difluorophenylthio)-4-nitrobenzoyl chloride (1.2 g) in ether (8 ml) was added to a stirred mixture of 40% methylamine (2 ml), water (8 ml) and ether (5 ml) at 0° to 5° C. The mixture was stirred at the same temperature for 1 hour and at room temperature for 1 hour. The organic layer was separated, washed with water, dried and concentrated. The oily residue was crystallized from a mixture of ethyl acetate and hexane to give crystals of N-methyl-3-(2,4-difluorophenylthio)-4-nitrobenzamide (0.7 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe oily residue was crystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-fd2484c9484e4fd3a033dfc31b01ef4f
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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