Methanol → HCID 67541677, compound

HRID 1747283Notes

Reaction equation

HRID 1747283 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:18][CH2:19][CH3:20])(=[O:17])[CH:15]=[CH2:16].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.CO>CN(C=O)C.C(OCC)(=O)C>[CH2:19]([O:18][C:14](=[O:17])[CH2:15][CH2:16][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])[CH3:20]

Participants

7

Reactant 4

HCID 887MethanolHCID 8821Ethyl AcrylateHCID 66854Benzyltrimethylammonium hydroxideHCID 1002781,3-Dihydro-1-(1-methylvinyl)-2H-benzimidazol-2-one

Product 1

HCID 67541677HCID 67541677, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-Isopropenyl-2-benzimidazolidinone (2.5 g, 14.4 mmol) in DMF (10 mL) were added ethyl acrylate (1.7 mL, 15.8 mmol) and benzyltrimethyl ammonium hydroxide in MeOH (1.4 g, 8.6 mmol). The resulting mixture was stirred at room temperature for 1.5 h. When the reaction was complete, the reaction mixture was diluted with ethyl acetate and washed with water (×4). The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 1:1 Hexanes:Ethyl acetate as an eluent to afford 3.0 g (76%) of the desired product along with methyl ester. Since the methyl ester was the major product, this product was used for the next reaction.

Workup

  1. washwashed with water (×4)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-d66fc98384b44672aac69269af99f6d7
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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