Benzaldehyde → 10-benzylidene-5H,10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-one

HRID 1290749노트

반응식

HRID 1290749 반응식
[CH:1]1[N:5]2[C:6]3[CH2:17][C:16]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[C:7]=3[NH:8][C:9](=[O:10])[C:4]2=[N:3][CH:2]=1.[OH-].[Na+].[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O.C(O)(=O)C>[CH:20](=[C:17]1[C:6]2[N:5]3[CH:1]=[CH:2][N:3]=[C:4]3[C:9](=[O:10])[NH:8][C:7]=2[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:16]1=2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

8

반응물 4

HCID 240BenzaldehydeHCID 962WaterHCID 14798Sodium HydroxideHCID 103535495H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

생성물 1

HCID 7034388410-benzylidene-5H,10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-one수율 1.6%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 176Acetic Acid용매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
20 °C

실험 절차

A suspension of 5.75 g of 5H,10H-imidazo-[1,2-a]indeno[1,2-e]pyrazin-4-one, 10 g of sodium hydroxide pellets and 125 mg of tetrabutylammonium bromide in 200 ml of dimethyl sulphoxide is stirred at a temperature in the region of 20° C. 3.18 g of benzaldehyde are then added and the stirring is continued for 18 hours at a temperature in the region of 20° C. The reaction mixture is poured into a mixture of water and ice (250 ml) and acidified with 100 ml of acetic acid. The solid formed is filtered off and the crude product is purified by two successive chromatographies on a column of silica with a mixture of dichloromethane and methanol (90/10 by volume). 0.13 g of 10-benzylidene-5H,10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-one is thus obtained, in the form of a yellow solid melting above 260° C. (Analysis % calculated C: 77.16, H: 4.21, N: 13.50, O: 5.14, % found C: 76.7, H: 3.7, N: 13.2).

후처리

  1. customThe solid formed
  2. filtrationis filtered off
  3. customthe crude product is purified by two successive chromatographies on a column of silica with a mixture of dichloromethane and methanol (90/10 by volume)

출처 및 근거

ORD 기록
ord-dde683bbfa194685896c70993f11c00e
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753657

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