Ammonium Chloride → Ethyl 4-amino-3-(2,4-difluorophenylthio)benzoate

HRID 1087175Notes

Reaction equation

HRID 1087175 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:18]=[CH:19][C:20]=1[N+:21]([O-])=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:21][C:20]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][C:10]=1[S:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 10359815Ethyl 3-(2,4-difluorophenylthio)-4-nitrobenzoate

Product 1

HCID 10040979Ethyl 4-amino-3-(2,4-difluorophenylthio)benzoateYield 109.7%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl 3-(2,4-difluorophenylthio)-4-nitrobenzoate (1.1 g), iron powder (1.1 g) and ammonium chloride (0.11 g) in ethanol (10 ml) and water (5 ml) was stirred and refluxed for 1 hour. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with water, dried and evaporated to give crystals of ethyl 4-amino-3-(2,4-difluorophenylthio)benzoate (1.1 g).

Workup

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

Sources & evidence

ORD record
ord-43e5049a3d9746408a2f3f8067a9e773
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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