<原報>Thiazoline 及び Thiazolidine 誘導体の合成 XIII : 2-Imino-3-methylcarbamoylthiazolidine 及び関連化合物の合成

概要

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As shown in Chart I A and I B the reaction between 2-amino-2-thiazoline (1) and an equimolar methylisocyanate (2a) under 20° gave the main product 2-imino-3-methylcarbamoylthiazolidine (3a) with some amount of isomeric 2-methylcarbamoylamino-2-thiazoline (4a) and they can be separated by chromatography. (3a) converted into stable isomeric (4a) by heating in benzene. The structure of (3a) was estimated chemicaly from the acidic hydrolysis of (3a). 2-Methylcarbamoylimino-3-methylcarbamoylthiazolidine (5a), 2-methylcarbamoylimino-3-methylthiocarbamoylthiazolidine (6) and 2-methylthiocarbamoyl-3-methylcarbamoylthiazolidine (7) were also synthesized. The reaction of 2-methylamino-2-thiazoline (9) with (2a) gave a monoadduct product having a molecular formula of C_6H_<11>N_3OS (m.p.39-40°) for which two compounds (10a, 11a) may be considered. The above product appears to be 2-methylimino-3-methylcarbamoylthiazolidine (10a) by obtaining the data of nuclear magnetic resonance (see Table IV), Ultraviolet spectrum (see Table I and Fig. I). As we reported previously, the reaction of (9) and methylisothiccyanate (2b) gave (10b) and did not give (11b). The same as the above, the reaction of (9) and (2a) gave only (10a) as a result, even though (2a) had stronger reactivity than (2b).
共立薬科大学の論文
1976-02-25