Ammonium Chloride → N-methyl-4-amino-3-(2,4-difluorophenylthio)benzamide

HRID 1087178Notes

Reaction equation

HRID 1087178 reaction equation
[CH3:1][NH:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[C:6]([S:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])[CH:5]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[CH3:1][NH:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([S:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])[CH:5]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 10471482N-methyl-3-(2,4-difluorophenylthio)-4-nitrobenzamide

Product 1

HCID 10334628N-methyl-4-amino-3-(2,4-difluorophenylthio)benzamideYield 126.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of N-methyl-3-(2,4-difluorophenylthio)-4-nitrobenzamide (0.68 g), iron powder (0.68 g) and ammonium chloride (68 mg) in ethanol (8 ml) and water (4 ml) was stirred and refluxed for 2 hours. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate, washed with water, dried and evaporated to give pale yellow crystals of N-methyl-4-amino-3-(2,4-difluorophenylthio)benzamide (0.78 g).

Workup

  1. temperaturerefluxed for 2 hours
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-53cc8826e84a4e6298839dce1f28f3ce
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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