HRID615706

反应详情

EQUATION

反应方程式

HRID 615706 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

1

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

  1. additionA mixture of 1.4 g
  2. concentrationThe mixture was then concentrated under reduced pressure
  3. customthe residue azeotroped twice with 30 ml
  4. customof cyclohexane to yield a colorless oil
  5. additionThe oil was then added dropwise to a cold
  6. additionsuspension of 1.2 g
  7. stirringAfter stirring for 35 minutes
  8. additionthe reaction mixture was poured onto ice-water
  9. customresulting in formation of a yellow solid, which
  10. customwas collected
  11. washwashed with water
  12. customair-dried
  13. custompurified
  14. additiona mixture of 2% ethyl acetate
  15. additionFractions containing the product
  16. customtriturated with ether