Sodium borohydride → 3,5-Difluoro-4-(4-thiomorpholinyl)aniline

HRID 895125Notes

Reaction equation

HRID 895125 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[C:6]([F:13])[C:5]=1[N:14]1[CH2:19][CH2:18][S:17][CH2:16][CH2:15]1>CO.C(OCC)(=O)C>[F:13][C:6]1[CH:7]=[C:8]([NH2:10])[CH:9]=[C:4]([F:3])[C:5]=1[N:14]1[CH2:15][CH2:16][S:17][CH2:18][CH2:19]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 120965924-(2,6-Difluoro-4-nitrophenyl)thiomorpholine

Product 1

HCID 218781383,5-Difluoro-4-(4-thiomorpholinyl)anilineYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium borohydride (285 mg, 7.5 mmol) was added to a stirring solution of NiCl2.6H2O (1.16 g, 5.0 mmol) and 4-(2,6-difluoro-4-nitrophenyl)thiomorpholine, obtain in Preparation 3, in methanol (30 mL). The reaction mixture was diluted with ethyl acetate (50 mL) after 0.5 h and the organic portion was washed with water (30 mL×2) followed by brine (30 mL) and dried over sodium sulfate. Evaporation of the volatiles yielded the title compound as light brown solid (400 mg, 70%).

Workup

  1. washthe organic portion was washed with water (30 mL×2)
  2. dry with materialdried over sodium sulfate
  3. customEvaporation of the volatiles

Sources & evidence

ORD record
ord-c29107fc5eed4d3ab83f72f1740f7bb4
Source dataset
uspto-grants-2005_07
Patent number
US06914058B2

Reaction notes

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