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Benzimidazole → 1-[2-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethyl]-1H-benzo[d]imidazole

HRID 2268506
ノート
印刷プレビュー

反応式

HRID 2268506 の反応式
I[CH2:2][CH2:3][CH:4]1[CH2:10][CH2:9][C:8]2[C:11]([O:21][CH3:22])=[C:12]([O:19][CH3:20])[C:13]([O:17][CH3:18])=[C:14]([O:15][CH3:16])[C:7]=2[CH2:6][CH2:5]1.[N:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[NH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O>[CH3:16][O:15][C:14]1[C:7]2[CH2:6][CH2:5][CH:4]([CH2:3][CH2:2][N:23]3[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[N:25]=[CH:24]3)[CH2:10][CH2:9][C:8]=2[C:11]([O:21][CH3:22])=[C:12]([O:19][CH3:20])[C:13]=1[O:17][CH3:18]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 5798BenzimidazoleHCID 10340Sodium CarbonateHCID 183485187-(2-Iodoethyl)-1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cycloheptene

生成物 1

HCID 183485591-[2-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethyl]-1H-benzo[d]imidazole収率 32.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6228
Dimethylformamide
溶媒

反応条件

温度
70 °C

実験手順

A mixture of 7-(2-iodoethyl)-1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cycloheptene (1.50 g), benzimidazole (443 mg), and sodium carbonate (760 mg) in DMF (15 ml) was stirred at 70° C. for 8 hr. The reaction mixture was diluted with water and extracted with combined solution of ethyl acetate and THF. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo and the residue was diluted with diethylether and the resultant crystals were removed by filtration. The filtrate was concentrate in vacuo. The residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=1:2) and then with recrystallization from hexane-ethyl acetate to obtain the entitled compound (480 mg).

後処理

  1. extractionextracted with combined solution of ethyl acetate and THF
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. customdried
  4. customThe solvent was removed in vacuo
  5. additionthe residue was diluted with diethylether
  6. customthe resultant crystals were removed by filtration
  7. concentrationThe filtrate was concentrate in vacuo
  8. customThe residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=1:2)
  9. customwith recrystallization from hexane-ethyl acetate

出典と根拠

ORDレコード
ord-ad73347caa454111b59c1ad69d1b0a9c
出典データセット
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06326369B1

反応ノート

読み込み中…

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