S-Methylisothiourea sulfate

A mixture of 85 parts of S-methylisothiourea sulfate, 6.05 parts of methyl chloroformate in... 

SZABO, C., SOUTHAN, G. J., Thiemermann, C, Beneficial effects and improved survival in rodent models of septic shock with S-methylisothiourea sulfate, a potent and selective inhibitor of inducible nitric oxide synthase, Proc. Natl. Acad. Sci. USA 91 (1994), p. 12472-12476... 

Guanethidine and Ismelin. The sulfate salt (m.p. 276-281 °C) can be prepared by the reaction of C1CH2CN with (1), followed by reduction of the nitrile group with LAH and treatment with S- methylisothiourea sulfate. An extensive literature exists on the pharmacology of this compound. 

A mixture of 89 parts of S-methylisothiourea sulfate, 6.05 parts of methyl chloroformate in 7 parts of water is cooled, and at a temperature of 5°C to 10°C, sodium hydroxide solution 25% is added until pH equals 8. Then there are added successively 6.4 parts of acetic acid, 2.6 parts of sodium acetate and 8.9 parts of 3,4-diamino-4 -fluorobenzophenone hydrochloride and the whole is stirred while heating at 85°C for 45 minutes (during this reaction time, water and 2-propanol is added). The precipitated product is filtered off, washed with methanol and recrystallized from a mixture of 200 parts of acetic acid and 80 parts of methanol, yielding methyl N-[5(6)-p-fluorobenzoyl-2-benzimidazolyl] carbamate MP > 260°C. 

Recent work has made use of the reaction of compounds of the types 133124 124a and 134 (Y = S or O)123 with 129 to give 126. The 6-amino compound (126, R = NH2) has been prepared by fusion of 129 and S-methylisothiourea sulfate,129 while fusion of 129 and earbodi-imides gave rise to compounds of the type 126 (R = NHR ).129 The bis diazepine 126 (R = another dibenzodiazepine unit) has been prepared.1354... 

Derivatives. Procedures are formulated for the preparation of S-methylisothiourea sulfate" and guanidinoacetic acid."... 

Imino-l,3-thiazetidine 83 was used as precursor in the synthesis of triazine 85 (Scheme 36) [74], Reaction of 83 with hifluoroacetic anhydride leads to 2-trifluoromethylimino-3-(4-chlorophenyl)-l,3-thiazetidine 84, the treatment of 84 with S-methylisothiourea sulfate results in trifluoromethyl substituted triazine 85. 

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