Ammonium Chloride → N-ethyl4-amino-3-(2,4-difluorophenylthio)benzamide

HRID 1087188Notes

Reaction equation

HRID 1087188 reaction equation
[CH2:1]([NH:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[C:7]([S:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])[CH:6]=1)[CH3:2].[Cl-].[NH4+]>C(O)C.O.[Fe]>[CH2:1]([NH:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[C:7]([S:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])[CH:6]=1)[CH3:2]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 11724674N-ethyl-3-(2,4-difluorophenylthio)4-nitrobenzamide

Product 1

HCID 10086583N-ethyl4-amino-3-(2,4-difluorophenylthio)benzamideYield 101.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of N-ethyl-3-(2,4-difluorophenylthio)4-nitrobenzamide (0.92 g), iron powder (0.92 g) and ammonium chloride (92 mg) in ethanol (10 ml) and water (5 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 an oil of N-ethyl4-amino-3-(2,4-difluorophenylthio)benzamide (0.85 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-b5549621b73e4797ab287d9edacddb57
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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