反应 #76551

反应方程式

amide

N-(2-benzylthiazolo[4,5-c]quinolin-4-yl)trichloroacetamide

Sodium methoxide

Hydrochloric acid

→

2-benzylthiazolo[4,5-c]quinolin-4-amine hydrochloride

溶剂

methanol

methanol

isopropanol

反应条件

后处理

1. 1
   温度The reaction mixture was heated on a steam bath for 30 minutes
2. 2
   其他The resulting precipitate was isolated by filtration
3. 3
   workup.DISSOLUTIONall of the solid dissolved initially
4. 4
   其他A white solid crystallized out
5. 5
   其他This material was isolated by filtration
6. 6
   洗涤washed with isopropanol
7. 7
   其他dried

实验过程

Trichloroacetyl isocyanate (1.2 mL, 10.3 mmol) was added to a solution of 2-benzylthiazolo[4,5-c]quinoline-5N-oxide (2.0 g, 6.8 mmol) in dichloromethane (100 mL). The reaction mixture was stirred at ambient temperature for 2 hours and then concentrated to provide crude N-(2-benzylthiazolo[4,5-c]quinolin-4-yl)trichloroacetamide. The amide was dissolved in methanol. Sodium methoxide (1 equivalent) was added. The reaction mixture was heated on a steam bath for 30 minutes and then allowed to cool to ambient temperature. The resulting precipitate was isolated by filtration and then suspended in a mixture of methanol and isopropanol. Hydrochloric acid (1 equivalent) was added and all of the solid dissolved initially. A white solid crystallized out. This material was isolated by filtration, washed with isopropanol and then dried to provide 1.5 g of 2-benzylthiazolo[4,5-c]quinolin-4-amine hydrochloride, m.p. 152-155° C. Analysis: Calculated for: C17H13N3S.HCl: %C, 62.28; %H, 4.30; %N, 12.82; Found: %C, 62.05; %H, 4.23; %N, 12.82.

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