Ethanol → 3-(3,5-Di-tert-butyl-4-hydroxyphenyl)-5,6-diphenyl imidazo[2,1-b]thiazole

반응식

[Na].[C:2]1([C:8]2[N:9]=[C:10]([SH:19])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([C:24]1[CH:25]=[C:26]([CH:31]=[C:32]([C:34]([CH3:37])([CH3:36])[CH3:35])[CH:33]=1)[C:27](=O)[CH2:28]Br)([CH3:23])([CH3:22])[CH3:21].C([OH:40])C>>[C:20]([C:24]1[CH:25]=[C:26]([C:27]2[N:9]3[C:8]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[C:12]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:11]=[C:10]3[S:19][CH:28]=2)[CH:31]=[C:32]([C:34]([CH3:37])([CH3:36])[CH3:35])[C:33]=1[OH:40])([CH3:23])([CH3:22])[CH3:21]

참가 물질

반응물 4

HCID 702Ethanol

HCID 5360545Sodium

HCID 202223723,5-Di-tert-butylphenacyl bromide

HCID 178527825HCID 178527825, 화합물

생성물 1

HCID 137543273-(3,5-Di-tert-butyl-4-hydroxyphenyl)-5,6-diphenyl imidazo[2,1-b]thiazole

실험 절차

In 20 ml of ethanol was dissolved 0.11 g of metallic sodium and after adding 1 g of 4,5-diphenyl-2-mercaptoimidazole to the solution followed by stirring several minutes, 1 g of 3,5-di-tert-butylphenacyl bromide was added thereto followed by stirring for one hour at room temperature. The reaction mixture was concentrated udner reduced pressure and then water was added to the residue. The crystals thus formed were recovered by filtration, dried, dissolved in 20 ml of phosphorus oxychloride, and the solution was refluxed for 14 hours. The reaction mixture was concentrated under reduced pressure and after adding water to the residue followed by neutralization with potassium carbonate, the product was extracted with chloroform. The extract was dried and concentrated. The residue was subjected to silica gel column chromatography and the product was eluted with chloroform. The crude crystals thus obtained were recrystallized from ethanol to provide 0.8 g of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-5,6-diphenyl imidazo[2,1-b]thiazole.