Water → HCID 178509604, compound

HRID 498966

Reaction equation

HRID 498966 reaction equation
[SH:1][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].O>CS(C)=O>[S:1]([C:6]1[CH:7]=[C:8]([C:10]2[C:11]([C:15]([F:16])([F:17])[F:18])=[N:12][NH:13][CH:14]=2)[CH:9]=[CH:2][C:3]=1[C:4]#[N:5])[C:2]1[CH:9]=[C:8]([C:10]2[C:11]([C:15]([F:16])([F:18])[F:17])=[N:12][NH:13][CH:14]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 962WaterHCID 178509603HCID 178509603, compound

Product 1

HCID 178509604HCID 178509604, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3.0 g (11.1 mmol) of 2-mercapto-4-(3-trifluoromethylpyrazolyl)benzonitrile in 5 ml of dimethyl sulfoxide was stirred at 50° C. for 2 hours. The reaction mixture was cooled to room temperature and poured into 50 ml of water, and the organic matters were extracted with 20 ml of ethyl acetate twice. The ethyl acetate layers were combined, then washed with 30 ml of water twice and dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. Purification of the residue afforded 1.3 g of 1,1′-thiodi-[2-cyano-5-(3-trifluoromethylpyrazolyl)benzene] (yield 42.4%) as a yellow solid, which was used in Example 2 (3) as the starting material.

Workup

  1. extractionthe organic matters were extracted with 20 ml of ethyl acetate twice
  2. washwashed with 30 ml of water twice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe ethyl acetate was distilled off under reduced pressure
  5. customPurification of the residue

Sources & evidence

ORD record
ord-8094bbf29fee4179a0c582e68c43aa00
Source dataset
uspto-grants-2010_08
Patent number
US07767626B2

Linked notes

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