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N-Methyl-2-phenacylthioirnidazoline (2) and the corresponding hydrobromide (1 ) exist largely in bicyclic forms owing to interactions between the carbonyl group and a ring nitrogen atom.THE tautomerism of 2-phenacylthioimidazolinium bromides has been discussed.l It was thought that compounds of this class with substituents on the ring nitrogen atom would not exhibit amino-carbinol-ketoimine tautomerismJa and consequently l-methyl-2phenacylthioimidazolinium bromide (1) was prepared. This compound showed i.r. carbonyl absorption, but lH n.m.r. spectroscopy showed that only 25% existed as the keto-form (1B) and that the remainder probably exists as a cyclic form (1A or C). Treatment of the hydrobromide (1) with ammonia gave a base (2) with analytical figures corresponding to C,,H,,N,OS but its i.r. spectrum did not show a carbonyl band. Treatment of the base (2) with hydrobromic acid gave a salt which differed from the original hydrobromide, and analysis showed that loss of a molecule of water had occurred. By analogy with the formation of 3-phenyl-5,6-dihydrothiazolo-[2,3-d]thiazoliuni bromide from 2-phenacylthiothiazolinium brornideJ3p4 this hydrobromide should be 4 (or 7)methyl-3-phenyl-5,6-dihydroimidazo [2, 1 -b] thiazolium Laboratories, Lower Road, Widnes, Lancs.

By varying the conditions of reaction between the silver salt of uracil and 2,3,4,6-tetra-O-acetylglucopyranosyl bromide (ABG) and from a study of the rearrangement of uracil 0 ( 2 ) 0 ( 6 ) -and N(3)0(6)-bisglucosides it has been shown that these compounds are intermediates in the formation of the uracil N-glucosides, and that a competitive route must exist for the formation of uracil N(3)-glucoside. In the case of thymine, the formation of the N(3)-glucoside from the 0(2)0(6)-bisglucoside via the N(3)0(6)-bisglucoside is confirmed.

Alkylhydrazines as Monamine Oxidase Inhibitors 63 Method B.--To a warm solution of 0.02 mole of an ethyl Narylsulfonylcarbamate in 75 ml. of toluene was added, dropwise, with stirring, a solution of 0.022 mole of the desired amine in 25 ml. of toluene. The mixture was refluxed for 3 hr. and cooled.If the product crystallized, it was isolated by filtration; otherwise, the toluene was removed under reduced pressure. The product was crystallized from dilute ethanol, with acidification with 5% hydrochloric acid just prior to cooling. Further purification was carried out as indicated in the tables.4-Methylsulfinylbenzenesulfonamide.-To a solution of 12 g. (0.05 mole) of 4-methylmercaptobenzenesulfonamide in 200 ml. of acetic acid was added, portionwise, 5.7 g. (0.05 mole) of 30% ti4

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