Ammonium Chloride → HCID 59497660, compound

HRID 1747362

Reaction equation

HRID 1747362 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 59497660HCID 59497660, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-00b6d349062b4aa79ec4595566599d5b
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Linked notes

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