Water → HCID 178509641, compound

HRID 25290Notes

Reaction equation

HRID 25290 reaction equation
Cl[C:2]1[CH:9]=[C:8]([C:10]2[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][NH:12][N:11]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[F:19][C:20]([F:24])([F:23])[CH2:21][SH:22].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:19][C:20]([F:24])([F:23])[CH2:21][S:22][C:2]1[CH:9]=[C:8]([C:10]2[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][NH:12][N:11]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 41339242,2,2-TrifluoroethanethiolHCID 178509640HCID 178509640, compound

Product 1

HCID 178509641HCID 178509641, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.65 g (2.4 mmol) of 2-chloro-4-(4-trifluoromethylpyrazolyl)benzonitrile, 0.33 g (2.9 mmol) of 2,2,2-trifluoroethanthiol and 0.40 g (2.9 mmol) of potassium carbonate were stirred in 5 ml of N,N-dimethylformamide at room temperature overnight. The resulting reaction mixture was 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, 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 by silica gel column chromatography afforded 0.48 g of 2-(2,2,2-trifluoroethylthio)-4-(4-trifluoromethylpyrazolyl)benzonitrile (yield 57.1%) as a milk-white powder (m.p. 90-91° C.).

Workup

  1. customThe resulting reaction mixture
  2. extractionthe organic matters were extracted with 20 ml of ethyl acetate twice
  3. washwashed with 30 ml of water twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe ethyl acetate was distilled off under reduced pressure
  6. customPurification of the residue by silica gel column chromatography

Sources & evidence

ORD record
ord-c3b2522b0af94f7c9f5becc1e3909f4f
Source dataset
uspto-grants-2005_02
Patent number
US06858639B2

Reaction notes

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