Acetonitrile → [4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-acetonitrile
Reaction equation
Cl[CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[N:5][C:4]=1[CH3:18].C(=O)(O)[O-].[Na+].C(OCC)(=O)C.[C:30](#[N:32])C>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:18][C:4]1[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[S:7][C:3]=1[CH2:2][C:30]#[N:32]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Tetrabutylammonium cyanide (18.5 g, 67 mmol) was added to a solution of 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole [15.0 g, 51 mmol; PCT Int. Appl. (2002), WO 0292590 A1] in acetonitrile (340 ml). The solution was stirred at ambient temperature for 16 h, saturated aqueous sodium bicarbonate solution/ice water 1/1 and ethyl acetate were added and the layers were separated. The aqueous layer was extracted with ethyl acetate, the combined organic layers were washed with ice water/brine 1/1, dried over sodium sulfate and the solvent was evaporated in vacuo to give a brown oil which was purified by column chromatography (silica gel, n-heptane/CH2Cl2) to yield 8.58 g (30 mmol, 59%) of the title compound as light yellow solid.
Workup
- customthe layers were separated
- extractionThe aqueous layer was extracted with ethyl acetate
- washthe combined organic layers were washed with ice water/brine 1/1
- dry with materialdried over sodium sulfate
- customthe solvent was evaporated in vacuo
- customto give a brown oil which
- customwas purified by column chromatography (silica gel, n-heptane/CH2Cl2)
Sources & evidence
- ORD record
- ord-46c57a0585d146dabdf3b89e5a81ecea
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07235572B2
Reaction notes
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