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Acetic Anhydride → (E)-5-Acetylamino-1-(2-pyridyl)-2-styryl-1H-benzimidazole

HRID 382561
ノート
印刷プレビュー

反応式

HRID 382561 の反応式
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[C:7](/[CH:9]=[CH:10]/[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:8][C:4]=2[CH:3]=1.C(=O)(O)[O-].[Na+].[C:30](OC(=O)C)(=[O:32])[CH3:31]>>[C:30]([NH:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[C:7](/[CH:9]=[CH:10]/[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:8][C:4]=2[CH:3]=1)(=[O:32])[CH3:31]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 22736667(E)-5-Amino-1-(2-pyridyl)-2-styryl-1H-benzimidazole

生成物 1

HCID 22736648(E)-5-Acetylamino-1-(2-pyridyl)-2-styryl-1H-benzimidazole収率 61%

実験手順

(E)-5-Amino-1-(2-pyridyl)-2-styryl-1H-benzimidazole (199 mg, 0.64 mmol) was dissolved in acetic anhydride (2 ml) and the solution was allowed to maintain at room temperature for 30 mm. Then the reaction mixture was poured into saturated aqueous sodium bicarbonate solution (50 ml) and the aqueous mixture was extracted with ethyl acetate (100 ml). The organic extract was washed consecutively with water (50 ml) and brine (50 ml), dried (sodium sulfate) and concentrated in vacuo. The residual solids were purified by column chromatography (silica gel, 50 g; n-hexane/ethyl acetate (1/2)) and then recrystallized from ethyl acetate to afford 139 mg (61%) of the titled compound as yellow solids.

後処理

  1. extractionthe aqueous mixture was extracted with ethyl acetate (100 ml)
  2. extractionThe organic extract
  3. washwas washed consecutively with water (50 ml) and brine (50 ml)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customThe residual solids were purified by column chromatography (silica gel, 50 g; n-hexane/ethyl acetate (1/2))
  7. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-c44d60bd0d9140cbb0964e754ba5b8c0
出典データセット
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06310079B1

反応ノート

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