Hydrochloric Acid → HCID 67272164、化合物

HRID 1398734ノート

反応式

HRID 1398734 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.CO>[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

7

反応物 4

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

生成物 1

HCID 67272164HCID 67272164、化合物収率 79%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of methyl 2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate (35.9 g, 189 mmol) in tetrahydrofuran (700 mL) was added dropwise 3M solution of ethylmagnesium bromide in diethyl ether (374 mL, 1.12 mol), and the mixture was refluxed for 3 hr. After cooling, methanol (70 mL) was added dropwise at 0° C., and 1 N hydrochloric acid (1300 mL) was added at 0° C. The mixture was stirred at room temperature for 40 min, and the organic layer was separated and concentrated in vacuo. The aqueous layer was extracted with ethyl acetate (400 mL×2). The combined organic layer was concentrated in vacuo. The resulting solid was suspended in diisopropyl ether (70 mL)-water (10 mL)-ethyl acetate (40 mL), and the mixture was refluxed for 30 min. After cooling to room temperature, the resulting solid was collected by filtration and washed with diisopropyl ether to give the title compound (33.0 g, 150 mmol, 79%) cas a pale yellow solid.

後処理

  1. temperaturethe mixture was refluxed for 3 hr
  2. temperatureAfter cooling
  3. customthe organic layer was separated
  4. concentrationconcentrated in vacuo
  5. extractionThe aqueous layer was extracted with ethyl acetate (400 mL×2)
  6. concentrationThe combined organic layer was concentrated in vacuo
  7. temperaturethe mixture was refluxed for 30 min
  8. temperatureAfter cooling to room temperature
  9. filtrationthe resulting solid was collected by filtration
  10. washwashed with diisopropyl ether

出典と根拠

ORDレコード
ord-2f74e6348634476b832cc68985830810
出典データセット
uspto-grants-2014_12
特許番号
US08901141B2

反応ノート

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