反応 #62939

反応方程式

(±) N-(4,5,5a,6,7,8-hexahydro-6-methylthiazolo[4,5-f]quinolin-2-yl)-2-methylpropanamide

cyanogen bromide

chloroform

chloroform

→

title compound

(±) 4,5,5a,6,7,8-Hexahydrothiazolo[4,5-f]quinolin-2-amine, dihydrochloride

反応条件

後処理

1. 1
   濃縮The solution is concentrated
2. 2
   温度the resultant yellow oily solid is refluxed in 150 ml of 10% hydrochloric acid for 12 hours
3. 3
   温度The solution is cooled
4. 4
   抽出extracted into chloroform
5. 5
   抽出The chloroform extract
6. 6
   乾燥is dried (magnesium sulfate)
7. 7
   ろ過filtered
8. 8
   濃縮concentrated to a brown oil
9. 9
   その他Medium pressure chromatography (silica gel, 5% methanol--2% ammonium hydroxide--93% ethyl acetate) followed by salt formation and recrystallization from methanol/diethyl ether

実験手順

A solution of 5.00 g (17.15 mmol) of (±) N-(4,5,5a,6,7,8-hexahydro-6-methylthiazolo[4,5-f]quinolin-2-yl)-2-methylpropanamide (Example 15) in 150 ml of chloroform containing 20.6 ml (19.25 mmol) of a 1.07 M solution of cyanogen bromide in chloroform is refluxed, under nitrogen, for 12 hours. The solution is concentrated and the resultant yellow oily solid is refluxed in 150 ml of 10% hydrochloric acid for 12 hours. The solution is cooled, basified with ammonium hydroxide and extracted into chloroform. The chloroform extract is dried (magnesium sulfate), filtered and concentrated to a brown oil. Medium pressure chromatography (silica gel, 5% methanol--2% ammonium hydroxide--93% ethyl acetate) followed by salt formation and recrystallization from methanol/diethyl ether affords the title compound as a tan solid; mp 277°-279° C. (dec.).

出典