反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
PROCEDURE
实验过程
A mixture of 1.4 g. of 2-methylhexanoic acid (10.8 mmol.) and 3 ml. of thionyl chloride (41.1 mmol.) in 20 ml. of Skellysolve B was refluxed on a steam bath for five hours. The mixture was then concentrated under reduced pressure and the residue azeotroped twice with 30 ml. of cyclohexane to yield a colorless oil. The oil was then added dropwise to a cold, stirred suspension of 1.2 g. of 7-chloro-4-(4-chlorophenyl)-2-(hydroxymethyl)-5H-pyrido[3,4-b][1,4]benzothiazin-3(2H)-one (3.1 mmol.) in 20 ml. of pyridine. After stirring for 35 minutes, the reaction mixture was poured onto ice-water and allowed to stand for 16 hours at room temperature, resulting in formation of a yellow solid, which was collected, washed with water, air-dried, then purified using flash chromatography on silica gel, employing a mixture of 2% ethyl acetate: 98% methylene chloride as the eluent. Fractions containing the product were combined and triturated with ether to yield 7-chloro-4-(4-chlorophenyl)-2-[(2-methyl-1-oxohexyloxy)methyl]-5H-pyrido[3,4-b][1,4]benzothiazin-3(2H)-one as a yellow crystalline solid (1.17 g; 76% yield) having the structural formula, ##STR19## a melting point in the range of 140°-146° C. and the following elemental analysis:
WORKUP
后处理
- additionA mixture of 1.4 g
- concentrationThe mixture was then concentrated under reduced pressure
- customthe residue azeotroped twice with 30 ml
- customof cyclohexane to yield a colorless oil
- additionThe oil was then added dropwise to a cold
- additionsuspension of 1.2 g
- stirringAfter stirring for 35 minutes
- additionthe reaction mixture was poured onto ice-water
- customresulting in formation of a yellow solid, which
- customwas collected
- washwashed with water
- customair-dried
- custompurified
- additiona mixture of 2% ethyl acetate
- additionFractions containing the product
- customtriturated with ether