Sodium Cyanide → [2-(4-Isopropyl-phenyl)-thiazol-4-yl]-acetonitrile

HRID 394239Notes

Reaction equation

Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:16])[CH3:15])=[CH:10][CH:9]=2)[S:6][CH:7]=1.C(C1C=CC([C:24]([NH2:26])=S)=CC=1)(C)C.ClCC(CCl)=O.[C-]#N.[Na+]>CS(C)=O.O>[CH:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[S:6][CH:7]=[C:3]([CH2:2][C:24]#[N:26])[N:4]=2)=[CH:9][CH:10]=1)([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 40 °C

Procedure

14.5 g (57.6 mmol) of 4-chloromethyl-2-(4-isopropyl-phenyl)-thiazole (prepared from 4-isopropyl-thiobenzamide and 1,3-dichloroacetone in analogy to the procedure described in example 4 a]) and 4.08 g (83.4 mmol) of sodium cyanide in 50 ml of dimethyl sulfoxide were stirred at 40° C. for 2 hours. Then, the reaction mixture was poured into a mixture of ice and water and was subsequently extracted with 3 portions of 75 ml of tert-butyl methyl ether. The combined organic phases were washed with water, then with brine and dried with anhydrous sodium sulfate. After evaporation of the solvent, 13.4 g (96% of theory) of [2-(4-isopropyl-phenyl)-thiazol-4-yl]-acetonitrile were obtained as brown solid.

Workup

extractionwas subsequently extracted with 3 portions of 75 ml of tert-butyl methyl ether
washThe combined organic phases were washed with water
dry with materialwith brine and dried with anhydrous sodium sulfate
customAfter evaporation of the solvent

Sources & evidence

ORD record: ord-6febcf5681e248c295525a601d837e59
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809110B2

Reaction notes

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