Aminosulfonylations

Famotidine. Also known as Pepcid, famotidine [76824-35-6] (AT-(aminosulfonyl)-3-([[2-[(diaminomethylene) amino]-4-thia2olyl] methyl]thio)propariimidamide (2) is a white to pale yellow crystalline compound, freely soluble in glacial acetic acid, slightly soluble in methanol, very slightly soluble in water, and practically insoluble in ethanol. It may be prepared by the method described in Reference 3. 

Therapeutic Function Carbonic anhydrase inhibitor, diuretic, treatment of glaucoma Chemical Name N-[5-(aminosulfonyl)-1,3,4-thiadiazol-2-yl] acetamide Common Name —... 

Chemical Name 3-(aminosulfonyl)-5-(butylamino)-4-phenoxybenzoic acid Common Name —... 

A mixture consisting of 4 grams of 1,2,3,4-tetrahydro-4,4-dimethyl-7-methoxy-isochromane-dione-(1,3) (MP 95° to 97°C), 2.53 grams of 4-aminosulfonyl-phenyl-(2)-ethylamine and 150 ml of xylene was heated for 2 hours at its boiling point in an apparatus provided with a water separator. Thereafter, the reaction mixture was allowed to cool and was then vacuum-filtered, and the filter cake was recrystallized from n-propanoi in the presence of activated charcoal. 2.9 grams (58% of theory) of 1,2,3,4-tetrahydro-4,4-dimethyl-2-(p-amino-sulfonylphenyl-(2)-ethyl]-7-methoxy-isoquinolinedione-(1,3), MP 203° to 205°C, of the formula below were obtained. 

Chemical Name 3-(aminosulfonyl) 4-chloro-N-(2,3-dihydro-2-methyl-1 H-indol-Tyl)-benzamide... 

Chemical Name 5-(aminosulfonyl)-N-[(1-ethyl-2-pyrrolidinyl)methyl] -2-methoxybenz-amide... 

As shown by Heindel and Corley (1979), ring closure also takes place if the nucleophilic nitrogen is part of a heterocycle, as in the diazotization of 5-amino-3-methyl-2-H-l,2,4-benzothiadiazine-l, 1-dioxide (6.50). In the tricyclic compound 6.51 formed initially, the thiadiazinedioxide ring is opened rapidly in water, forming 1-acetyl-7-aminosulfonyl-l-i/-benzo-l,2,3-triazole (6.52). 

Aminosulfonyl-6-methyl-3,4-dihydro-2H- (benzo-1,2,4-thia-diazin)- ,1-dioxid 78% d.Th. 

Chlor-3-aminosulfonyl- 182 4-Chlor- -benzylimin 664 4-Chlor- -4-chlor-phenylimin 362 4-Chlor- -O-methyl-oxim 375... 

Aminosulfonyl-l-methyl- 680 4-Amino-l-thiocyanat- 685 2-Amino-5 -thiocyanat-1,3 -dimethyl-102... 

RN 636-54-4 MF C,4H2oClN303S MW 345.85 EINECS 211-261-7 CN s-3-(aminosulfonyl)-4-chloro-A-(2,6-dimethyl- l-piperidinyl)benzamide... 

CN 3-[[[2-[(aminoiminomethyl)amino]-4-thiazolyl]methyl]thio]-A (aminosulfonyl)propanimidamide... 

CN 5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoic acid... 

C]ftH,7ClN204S 16673-34-0) see Glibenclamide A -[2-[4-(aminosulfonyl)phenyl]ethyl]-3-ethyl-2,5-dihydro-... 

Aminosulfonyl ureas were constructed from a sulfonylcarbamate linkage (Scheme 31) [72], Reaction of chlorosulfonyl isocyanate (CSI) with Wang resin provided a chlorosulfonylcarbamate 63 which was then converted to substituted amino sulfonylcarbamate compounds by reaction with excess amines. The final aminosulfonyl urea products were cleaved from the resin by treatment with amines in HF at reflux temperature for overnight. 

---