反応 #833559

反応方程式

hydrogen

phenylisocyanate

sodium hydride

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

→

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

収率 60.0%

溶媒

tetrahydrofurane

tetrahydrofurane

tetrahydrofurane

反応条件

後処理

1. 1
   workup.ADDITIONwere added at −5° C
2. 2
   その他was quenched with ice/water and by addition of dilute HCl
3. 3
   抽出extracted with CH2Cl2 (2 times)
4. 4
   洗浄The combined CH2Cl2 extracts were washed
5. 5
   その他dried
6. 6
   濃縮concentrated
7. 7
   その他to give 6 g crude product
8. 8
   その他This material was recrystallized from ethanol

実験手順

To a suspension of 0.82 g (34 mmol) sodium hydride in 50 mL tetrahydrofurane was added at −5° C. under N2 a solution of 5.3 g (23 mmol) 3,4-dihydro-2,6-dimethyl-3-oxo-2H-thieno[3,2-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 4.8 g 3,4-dihydro-2,6-dimethyl-3-oxo-2H-thieno[3,2-e]-1,2-thiazine-4-carboxanilide 1,1-dioxide.

出典