Water → 2-Cyclobutylmethylthio-4-(3-trifluoromethylpyrazolyl)benzonitrile
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].[CH:19]1([CH2:23]Br)[CH2:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH:19]1([CH2:23][S:1][C:2]2[CH:9]=[C:8]([C:10]3[C:11]([C:15]([F:16])([F:18])[F:17])=[N:12][NH:13][CH:14]=3)[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH2:22][CH2:21][CH2:20]1Participants
Procedure
0.9 g (3.3 mmol) of 2-mercapto-4-(3-trifluoromethylpyrazolyl)benzonitrile, 0.5 g (3.3 mmol) of cyclobutylmethyl bromide and 0.55 g (4.0 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, 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 by silica gel column chromatography afforded 0.24 g of 2-cyclobutylmethylthio-4-(3-trifluoromethylpyrazolyl)benzonitrile (yield 21.2%) as a pale yellow powder (m.p. 102-103° C.).
Workup
- customThe resulting reaction mixture
- extractionthe organic matters were extracted with 20 ml of ethyl acetate twice
- washwashed with 30 ml of water twice
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe ethyl acetate was distilled off under reduced pressure
- customPurification of the residue by silica gel column chromatography
Sources & evidence
- ORD record
- ord-65b1e3c1277e41a58e8553a971b7cfde
- Source dataset
- uspto-grants-2003_01
- Patent number
- US06509354B1
Reaction notes
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