반응 #54407

반응 방정식

3-chloro-1,2-benzisothiazole 1,1-dioxide

4-[(1,1-Dioxo-1,2-benzisothiazol-3-yl)amino]butanoic acid, ethyl ester

glycine ethyl ester, hydrochloride

triethylamine

→

2-[(1,1-dioxo-1,2-benzisothiazol-3-yl)amino]acetic acid, ethyl ester

용매

dioxane

반응 조건

후처리

1. 1
   기타The dioxane is evaporated
2. 2
   세척is washed with water (2 x)
3. 3
   기타evaporated
4. 4
   기타The residue 2-[(1,1-dioxo-1,2-benzisothiazol-3-yl)amino]acetic acid, ethyl ester is recrystallized once from 150 ml of methanol/water (1:1) and once from 200 ml

실험 절차

15.0 g. (74.4 mM) of 3-chloro-1,2-benzisothiazole 1,1-dioxide (prepared as in Example 1), 10.4 g. (74.4 mM) of glycine ethyl ester, hydrochloride and 20.4 ml. (148.8 mM) of triethylamine are refluxed in 250 ml of dioxane for 2 hours. The dioxane is evaporated and the residue is taken up in chloroform which is washed with water (2 x) and evaporated. The residue 2-[(1,1-dioxo-1,2-benzisothiazol-3-yl)amino]acetic acid, ethyl ester is recrystallized once from 150 ml of methanol/water (1:1) and once from 200 ml. of water to give 2-[(1,1-dioxo-1,2-benzisothiazol-3-yl)amino]acetic acid, ethyl ester as yellow needles, yield 14.35 g., m.p. 166°-167°.

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