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

HRID 1290749ノート

反応式

HRID 1290749 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 176Acetic Acid溶媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
20 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-dde683bbfa194685896c70993f11c00e
出典データセット
uspto-grants-1998_05
特許番号
US05753657

反応ノート

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