Tiopinac
硫平酸Chemical Name: 2-(11-Oxo-6,11-dihydrodibenzo[b,e]thiepin-3-yl)acetic acid
CAS No. 61220-69-7
项目整合开发状态: Not Determined
项目研究机构:
合成路线:The esterification of 2-nitroterephthalic acid (I) with isopropanol by means of dry HCl gives the corresponding dusoproyl ester (II),which by reaction with benzylmercaptane by means of NaH in DMF yields diisopropyl 2-benzylthioterephthalate (III).This compound is hydrolyzed with KOH in refluxing methanol affording the correspon-ding acid (IV),which is converted into its diacid chloride (V) by treatment with refluxing SOCl2.The cyclization of (V) with AlCl3 in methylene chloride - nitromethane affords 6,11-dihydrodibenzo[b]thiepin-11-one-3-carbonyl chloride (VI),which is treated with diazomethane in ether - methylene chloride to yield the 3-diazoacetyl derivative (VII).The Arndt-Eister reaction of (VII) with silver benzoate in refluxing methanol affords methyl 6,11-dihydrodibenzo[b,e]thiepin-11-one-3-acetate (VIII),which is finally hydrolyzed with KOH in refluxing methanol.
📌 参考资料/链接：
参考文献标题:6,11-Dihydrodibenzothiepin-11-ones,compositions and uses thereof
文献作者:Ackrell,J.(Syntex (USA),Inc.)
参考来源:US 4000308
📄 详细内容
合成路线:The esterification of 2-nitroterephthalic acid (I) with isopropanol by means of dry HCl gives the corresponding dusoproyl ester (II),which by reaction with benzylmercaptane by means of NaH in DMF yields diisopropyl 2-benzylthioterephthalate (III).This compound is hydrolyzed with KOH in refluxing methanol affording the correspon-ding acid (IV),which is converted into its diacid chloride (V) by treatment with refluxing SOCl2.The cyclization of (V) with AlCl3 in methylene chloride - nitromethane affords 6,11-dihydrodibenzo[b]thiepin-11-one-3-carbonyl chloride (VI),which is treated with diazomethane in ether - methylene chloride to yield the 3-diazoacetyl derivative (VII).The Arndt-Eister reaction of (VII) with silver benzoate in refluxing methanol affords methyl 6,11-dihydrodibenzo[b,e]thiepin-11-one-3-acetate (VIII),which is finally hydrolyzed with KOH in refluxing methanol.
参考文献标题:Tiopinac
文献作者:Castar,J.; Leeson,P.
参考来源:Drugs Fut 1978,3(12),896
产品链接: CAS No. 61220-69-7››