반응 #833558

반응 방정식

hydrogen

phenylisocyanate

sodium hydride

3,4-dihydro-2,6-dimethyl-3-oxo-2H-thieno[2,3-e]-1,2-thiazine 1,1-dioxide

→

3,4-dihydro-2,6-dimethyl-3-oxo-2H-thieno[2,3-e]-1,2-thiazine-4-carboxanilide 1,1-dioxide

수율 69.0%

용매

tetrahydrofurane

tetrahydrofurane

tetrahydrofurane

반응 조건

후처리

1. 1
   workup.ADDITIONwere added at −5° C
2. 2
   기타was quenched with ice/water and by addition of dilute HCl
3. 3
   추출extracted with CH2Cl2 (2 times)
4. 4
   세척The combined CH2Cl2 extracts were washed
5. 5
   기타dried
6. 6
   농축concentrated
7. 7
   기타to give 6 g crude product
8. 8
   기타This material was recrystallized from ethanol

실험 절차

To a suspension of 0.78 g (32.5 mmol) sodium hydride in 50 mL tetrahydrofurane was added at −5° C. under N2 a solution of 5 g (21.6 mmol) 3,4-dihydro-2,6-dimethyl-3-oxo-2H-thieno[2,3-e]-1,2-thiazine 1,1-dioxide in 50 mL tetrahydrofurane. After termination of the hydrogen formation 6.5 g (55 mmol) phenylisocyanate dissolved in 50 mL tetrahydrofurane were added at −5° C. After stirring at room temperature the resulting mixture was quenched with ice/water and by addition of dilute HCl and then extracted with CH2Cl2 (2 times). The combined CH2Cl2 extracts were washed, dried and concentrated to give 6 g crude product. This material was recrystallized from ethanol to give 5.2 g 3,4-dihydro-2,6-dimethyl-3-oxo-2H-thieno[2,3-e]-1,2-thiazine-4-carboxanilide 1,1-dioxide.

출처