Ammonium Chloride → 5-(4-Fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-2-thiophenamine

HRID 1899089Notes

Reaction equation

HRID 1899089 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([N+:23]([O-])=O)=[CH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([NH2:23])=[CH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 106433092-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)-5-nitrothiophene

Product 1

HCID 104978555-(4-Fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-2-thiophenamineYield 81.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-nitrothiophene (3.6 g), iron powder (3.6 g) and ammonium chloride (0.36 g) in ethanol (58 ml) and water (22 ml) was stirred and refluxed for 1 hour. The insoluble was filtered and washed with N,N-dimethylformamide (40 ml). The filtrate was concentrated. The residue was triturated with water, filtered, and washed with water and ethanol to give a pale yellow powder of 5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-2-thiophenamine (2.7 g).

Workup

  1. temperaturerefluxed for 1 hour
  2. filtrationThe insoluble was filtered
  3. washwashed with N,N-dimethylformamide (40 ml)
  4. concentrationThe filtrate was concentrated
  5. customThe residue was triturated with water
  6. filtrationfiltered
  7. washwashed with water and ethanol

Sources & evidence

ORD record
ord-06d1d7c511704ab3b35da299a4a4bf1b
Source dataset
uspto-grants-1996_11
Patent number
US05571810

Reaction notes

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