Cyanomethyl carbamimidothioate--hydrogen chloride (1/1) → HCID 14456852, compound

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Reaction Conditions

Reaction Steps

In 10 ml of dimethylformamide is suspended 0.976 g of S-cyanomethylisothiourea hydrochloride prepared according to the method described in Japanese Published Unexamined Patent Application No. 50-154279. Under cooling at -35° C. and stirring, 2.73 g of 28% (w/w) sodium methylate solution is added dropwise, after which the mixture is stirred at -40° C. to -35° C. for 10 minutes. Then, a solution of 3.94 g of ethyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(2-iodoethoxyimino)acetate in 10 ml of dimethylformamide is added at the same temperature. The mixture is stirred at or below -30° C. for 5 minutes and then under ice-cooling for 4 hours. The reaction mixture is poured into 400 ml of ice-water and extracted with ethyl acetate. The extract is washed with aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. To the solid residue is added a mixture of ether-petroleum ether (1:1) and the mixture is filtered to give 3.18 g of ethyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(2-cyanomethylthioethoxyimino)acetate as light yellow crystals.

Provenance & Evidence