반응 #1196538

반응 방정식

5-(3,5-Di-tert-butyl-4-hydroxybenzylidene)thiazolidin-4-one

chlorosulfonyl isocyanate

→

objective compound

수율 69.3%

N-carbamoyl-5-(3,5-di-tert-butyl-4-hydroxy-benzylidene)thiazolidin-4-one

수율 69.3%

용매

toluene

toluene

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   기타to obtain a transparent solution of orange color
3. 3
   기타was evaporated under reduced pressure
4. 4
   workup.ADDITION3.6 ml of mixed solution of acetic acid and water (2:1) was added
5. 5
   workup.ADDITIONpoured into ice-water, which
6. 6
   추출was subjected to extraction with dichloromethane
7. 7
   세척The obtained organic layer was washed with water and saturated brine
8. 8
   건조dried over magnesium sulfate
9. 9
   기타evaporated
10. 10
    기타The obtained residue was separated

실험 절차

5-(3,5-Di-tert-butyl-4-hydroxybenzylidene)thiazolidin-4-one (479 mg, 1.5 mmole) described in Kokai 62-42977 was suspended in dried toluene (3 ml), to which chlorosulfonyl isocyanate (144 μl; 1.65 mmole) was added with stirring under nitrogen atmosphere, to obtain a transparent solution of orange color. Furthermore, the solution was heated at 90° C. for 10 min., from which toluene was evaporated under reduced pressure, then 3.6 ml of mixed solution of acetic acid and water (2:1) was added thereto. The resulting mixture was heated at 90° C. for 10 min. and poured into ice-water, which was subjected to extraction with dichloromethane. The obtained organic layer was washed with water and saturated brine, dried over magnesium sulfate, and evaporated. The obtained residue was separated by using silica gel chromatography (chloroform:acetone=20:1), whereby 377 mg of the objective compound was obtained, which was recrystallized from ethanol-ether in 53% yield. The physical constants are described on Table 1.

출처