Water → HCID 178509603, compound

HRID 25303

Reaction equation

HRID 25303 reaction equation
Cl[C:2]1[CH:9]=[C:8]([C:10]2[C:11]([C:15]([F:18])([F:17])[F:16])=[N:12][NH:13][CH:14]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[S-2:19].[Na+].[Na+].O>CN(C)C=O>[SH:19][C:2]1[CH:9]=[C:8]([C:10]2[C:11]([C:15]([F:18])([F:17])[F:16])=[N:12][NH:13][CH:14]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 962WaterHCID 14804Sodium SulfideHCID 1785096022-Chloro-4-(3-trifluoromethylpyrazolyl) benzonitrile

Product 1

HCID 178509603HCID 178509603, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.0 g (18.4 mmol) of 2-chloro-4-(3-trifluoromethylpyrazolyl)benzonitrile in N,N-dimethylformamide was stirred together with 1.86 g (23.9 mmol) of sodium sulfide at 120° C. for 30 minutes. The reaction mixture was cooled to room temperature, mixed with 100 ml of water, washed with 30 ml of ethyl acetate, and the aqueous layer was adjusted at pH 5-6 with citric acid, and extracted with 50 ml of ethyl acetate twice. The ethyl acetate layers were combined, washed with 50 ml of water twice and dried over anhydrous magnesium sulfate. The ethyl acetate was distilled off under reduced pressure to obtain 2-mercapto-4-(3-trifluoromethylpyrazolyl)benzonitrile (yield 97.6%) as a pale yellow powder, which was used in Example 1 (2) as the starting material.

Workup

  1. washwashed with 30 ml of ethyl acetate
  2. extractionextracted with 50 ml of ethyl acetate twice
  3. washwashed with 50 ml of water twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe ethyl acetate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-65d3528a2c174145a0986568ff963a1a
Source dataset
uspto-grants-2005_02
Patent number
US06858639B2

Linked notes

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