含磺酰胺桥类染料中间体的合成与表征

Synthesis and Characterization of Dye Intermediates Containing Sulfonamide as Linking Group

合成了两种磺酰替苯胺类染料中间体3′-甲基-4,4′-二氨基苯磺酰替苯胺(Ⅳ)和2′-甲氧基-4,5′-二氨基苯磺酰替苯胺(Ⅶ)。合成步骤如下:(1)邻甲苯胺、对甲氧基苯胺的氨基保护后,分别与氯磺酸反应得3-甲基-4-乙酰氨基苯磺酰氯(Ⅰ)和2-甲氧基-5-乙酰氨基苯磺酰氯(Ⅴ);(2)对氨基乙酰苯胺(Ⅱ)分别与Ⅰ、Ⅴ在w(CH3COOH)=5%的醋酸中反应,所得缩合物水解得产品Ⅳ、Ⅶ。产品经过IR1、HNMR1、3CNMR、MS表征确定了结构。胺化反应优化条件均为:n(Ⅰ或Ⅴ)∶n(Ⅱ)=1.1∶1,反应温度45℃,反应时间2 h,产率分别为89.37%、87.68%。

3-Methyl-4-acetaminobenzenesulfonyl chloride （ Ⅰ ） was prepared from o-methylaniline by protecting the amino group and then reacting with chlorosulfonic acid. Then p-aminoacetanilide and Ⅰ in mole ratio 1：1.1 reacted in w（CH3COOH） = 5% acetic acid at 45 ℃ for 2 h, and their condensation product was hydrolyzed to give 3 ＇-methyl-4,4＇-diaminobenzenesulfonanilide in 89. 37% yield. Similarly, with p-methoxylaniline, 2-methoxy-5-acetaminobenzenesulfonyl chloride was prepared and converted to 2＇-methoxy-4,5＇-diaminobenzenesulfonanilide in 87.68% yield. Both products were charactered by IR,1HNMR, 13 CNMR and MS.