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Benzamidine → HCID 178514988、化合物

HRID 1716551
ノート
印刷プレビュー

反応式

HRID 1716551 の反応式
Br[CH2:2][C:3](=O)[CH2:4][CH2:5][CH2:6][N:7]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=[O:17].[C:19]([NH2:27])(=[NH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:20]1([C:19]2[NH:26][CH:2]=[C:3]([CH2:4][CH2:5][CH2:6][N:7]3[C:15](=[O:16])[C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[C:8]3=[O:17])[N:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
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

5

反応物 3

HCID 2332BenzamidineHCID 11430Potassium CarbonateHCID 139032932-(5-bromo-4-oxopentyl)-2,3-dihydro-1H-isoindole-1,3-dione

生成物 1

HCID 178514988HCID 178514988、化合物収率 67.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of 2-(5-bromo-4-oxo-pentyl)-isoindole-1,3-dione [CAS 41306-64-3] (12.4 g) in abs. DMF (50 ml) was added benzamidine 85% (5.65 g) and potassium carbonate (11.05 g). The reaction mixture was stirred at 80° C. for 4 h, concentrated under high vacuum, quenched with water and extracted with ethyl acetate. The organic phase washed with ice/water and brine, dried over magnesium sulphate and concentrated. The residue was purified by chromatography on silica gel using methylene chloride/methanol 2 and 5% as eluent. The product fractions were combined and evaporated to dryness to obtain 2-[3-(2-phenyl-1H-imidazol-4-yl)-propyl]-isoindole-1,3-dione (8.95 g) as a light yellow foam.

後処理

  1. concentrationconcentrated under high vacuum
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic phase washed with ice/water and brine
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel
  8. customevaporated to dryness

出典と根拠

ORDレコード
ord-fee02f59745d41d59ff7720e6c29ccbb
出典データセット
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07803819B2

反応ノート

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