Ammonium Chloride → HCID 59497660, 화합물

HRID 1747362노트

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HRID 1747362 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 59497660HCID 59497660, 화합물수율 55%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-00b6d349062b4aa79ec4595566599d5b
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150556B2

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