Hydrochloric Acid → HCID 67272164、化合物

HRID 1698568ノート

反応式

HRID 1698568 の反応式
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([O:13]C)=O)[C:4]=2[NH:3]1.[CH2:15]([Mg]Br)[CH3:16].[CH2:19](OCC)[CH3:20].Cl>O1CCCC1>[CH2:19]([C:11]([C:10]1[C:4]2[NH:3][C:2](=[O:1])[NH:6][C:5]=2[CH:7]=[CH:8][CH:9]=1)([OH:13])[CH2:15][CH3:16])[CH3:20]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2 回HCID 22745204Methyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-4-carboxylateHCID 178418443HCID 178418443、化合物2 回

生成物 1

HCID 67272164HCID 67272164、化合物収率 74.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of methyl 2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate (513 mg, 2.67 mmol) in tetrahydrofuran (5 mL) was added 3M solution of ethyl magnesium bromide in diethyl ether (3.6 ml, 10.7 mmol), and the mixture was stirred at room temperature for 1 hour and refluxed for 20 hours. Addition of 3M solution of ethyl magnesium bromide in diethyl ether (5.3 mL, 16.0 mmol) was followed by refluxing for 30 hours. The reaction mixture was acidified with 6 N hydrochloric acid and extracted with ethyl acetate (X2). The combined organic layer was washed with brine (X1), dried over sodium sulfate and concentrated in vacuo. The resulting solid was washed with diisopropyl ether to give 440 mg (2.00 mmol, 74.8%) of the title compound.

後処理

  1. temperaturerefluxed for 20 hours
  2. temperatureby refluxing for 30 hours
  3. extractionextracted with ethyl acetate (X2)
  4. washThe combined organic layer was washed with brine (X1)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. washThe resulting solid was washed with diisopropyl ether

出典と根拠

ORDレコード
ord-11e110a3290a46d4adf681b99dd37144
出典データセット
uspto-grants-2012_04
特許番号
US08163935B2

反応ノート

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