2H-1,2,4-BENZOTHIADIAZINE 1,1-DIOXIDES .2. A CONDENSATION OF 2-AMINOBENZENESULFONAMIDE WITH CHLOROALKYL ISOTHIOCYANATES

被引：7
作者：
CHERN, JW [1 ]
WU, YH [1 ]
LIU, KC [1 ]
机构：
[1] NATL DEF MED CTR,MED LABS,TAIPEI 10700,TAIWAN
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 1990年 / 27卷 / 05期
关键词：
D O I：
10.1002/jhet.5570270556
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A reaction of 2‐aminobenzenesulfonamide (1) with 2‐chloroethyl or 3‐chloropropyl isothiocyanate in isopropanol afforded 2‐(2′‐chloroethylthioureido)‐ and 2‐(3′‐chloropropylthioureido)benzenesulfonamides (2a,b) in 67% and 55% yield respectively. Treatment of 2a,b with triethylamine in methanol at room temperature furnished 3‐(2′‐aminoethylthio)‐ and 3‐(3′‐aminopropylthio)‐2H‐1,2,4‐benzothiadiazine 1,1‐dioxides (9a,b) in quantitative yield. Heating 2b to reflux in methanol under neutral conditions gave 9b but in the form of the hydrochloride 8b which could be converted into the free base 9b by treating with ammonia water. When compounds 2a,b were treated with triethylamine in methanol at elevated temperature, 3‐(2′‐mercaptoethylamino)‐ and 3‐(3′‐mercaptopropylamino)‐2H‐1,2,4‐benzothiadiazine 1,1‐dioxides (10a,b) were obtained in good yield. Alternatively, 10a,b could also be prepared from 9a,b in 95% and 77% yield respectively. Copyright © 1990 Journal of Heterocyclic Chemistry
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收藏
页码：1485 / 1488
页数：4
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