Studies on Vitamin B1 and Related Compounds. C

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Abstract
Application of ammonia to aqueous solution of thiamine base at room temperature results in desulfurization-substitution reaction with evolution of hydrogen sulfide, as reported in the preceding paper. Identity of this product with 1-[(2-methyl-4-amino-5-pyrimidinyl)methyl]-4-(2-hydroxyethyl)-5-methylimidazole (III) was clear from its chemical properties and the identity of the product (VII) from the thiamine homolog, 3-[(2-methyl-4-amino-5-pyrimidinyl)methyl]-4, 5-dimethylthiazolium chloride (VI), by its similar reaction with ammonia, with the product obtained from 2-methyl-4-amino-5-bromomethylpyrimidine salt (IV) and 4, 5-dimethylimidazole (VIII). However, the product obtained by Erlenmeyer and others from (IV) and 4-(2-hydroxyethyl)-5-methylimidazole (V) was not identical with (III) and it was considered that there is a possibility that a position isomer (III′) would be produced in nonsymmetric imidazole like (V). Therefore, synthesis of (III′) was carried out by the route shown in Chart 2.

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