Hydrochloric Acid → 2H-Benzimidazol-2-one, 4-(1-ethylpropyl)-1,3-dihydro-

HRID 1398735ノート

反応式

HRID 1398735 の反応式
[CH2:1]([C:3]([C:7]1[C:15]2[NH:14][C:13](=[O:16])[NH:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)(O)[CH2:4][CH3:5])[CH3:2].Cl>[Pd].C(O)(=O)C>[CH2:1]([CH:3]([C:7]1[C:15]2[NH:14][C:13](=[O:16])[NH:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH2:4][CH3:5])[CH3:2]

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 67272164HCID 67272164、化合物

生成物 1

HCID 672730032H-Benzimidazol-2-one, 4-(1-ethylpropyl)-1,3-dihydro-収率 81%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒

反応条件

温度
80 °C

実験手順

A mixture of 4-(1-ethyl-1-hydroxypropyl)-1,3-dihydro-2H-benzimidazol-2-one (32.9 g, 149 mmol), 10% palladium on carbon (50% wet; 3.3 g), concentrated hydrochloric acid (3 mL) and acetic acid (300 mL) was purged with hydrogen and stirred under balloon pressure hydrogen at 80° C. for 6 hr. The catalyst was removed by filtration, and the filter cake was washed with tetrahydrofuran. The filtrate was concentrated in vacuo. The residue was suspended in diisopropyl ether (25 ml), and the suspension was stirred at 70° C. for 30 min. n-Hexane (25 mL) was added to the suspension, cooled to room temperature and stirred for 30 min. The resulting solid was collected by filtration and washed with n-hexane to give the title compound (24.6 g, 120 mmol, 81%) as a colorless solid.

後処理

  1. customwas purged with hydrogen
  2. customThe catalyst was removed by filtration
  3. washthe filter cake was washed with tetrahydrofuran
  4. concentrationThe filtrate was concentrated in vacuo
  5. stirringthe suspension was stirred at 70° C. for 30 min. n-Hexane (25 mL)
  6. additionwas added to the suspension
  7. temperaturecooled to room temperature
  8. stirringstirred for 30 min
  9. filtrationThe resulting solid was collected by filtration
  10. washwashed with n-hexane

出典と根拠

ORDレコード
ord-d7c25e5c8a7649cc999d4a2fe44edb85
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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