Ammonium Chloride → HCID 59497660、化合物

HRID 1747362

反応式

HRID 1747362 の反応式
[C:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13])([CH3:3])=[CH2:2].[C:14]([O:21][CH2:22][CH3:23])(=[O:20])/[CH:15]=[CH:16]/[CH2:17][CH2:18][CH3:19].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[NH4+].[Cl-]>CN(C=O)C>[CH2:22]([O:21][C:14](=[O:20])[CH2:15][CH:16]([N:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:4]([C:1]([CH3:3])=[CH2:2])[C:5]1=[O:13])[CH2:17][CH2:18][CH3:19])[CH3:23]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 66854Benzyltrimethylammonium hydroxideHCID 1002781,3-Dihydro-1-(1-methylvinyl)-2H-benzimidazol-2-oneHCID 5364778Ethyl trans-2-hexenoate

生成物 1

HCID 59497660HCID 59497660、化合物収率 55%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1-isopropenyl-2-benzimidazolinone (2 g, 11.5 mmol) in DMF (10 mL) were added ethyl trans-2-hexenoate (2 g, 14 mmol) and the benzyltrimethylammonium hydroxide (40% in MeOH) (0.4 mL, 2.3 mmol) at room temperature. The solution was heated to 60 C for 12 hours. The solution was cooled down and sat.NH4Cl sol was added. The solution was extracted with EtOAc and the combined organic layer was dried with MgSO4 and filtered. The filtrate was concentrated and the residue was purified by CombiFlash with 20% EtOAc in Hexane to afford the desirable product 3-(3-Isopropenyl-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl ester (2 g, 55%) as an colorless oil.

後処理

  1. customat room temperature
  2. temperatureThe solution was heated to 60 C for 12 hours
  3. temperatureThe solution was cooled down
  4. extractionThe solution was extracted with EtOAc
  5. dry with materialthe combined organic layer was dried with MgSO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customthe residue was purified by CombiFlash with 20% EtOAc in Hexane

出典と根拠

ORDレコード
ord-00b6d349062b4aa79ec4595566599d5b
出典データセット
uspto-grants-2015_10
特許番号
US09150556B2

関連ノート

読み込み中…