Water → Ethyl 4-[2-oxo-3-(prop-1-en-2-yl)-2,3-dihydro-1H-benzimidazol-1-yl]butanoate

HRID 1381096Notes

Reaction equation

HRID 1381096 reaction equation
[CH3:1][C:2]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13])=[CH2:3].[H-].[Na+].Br[CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].O>CN(C)C=O>[CH3:3][C:2]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:5]1=[O:13])=[CH2:1]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 1002781,3-Dihydro-1-(1-methylvinyl)-2H-benzimidazol-2-one

Product 1

HCID 23323468Ethyl 4-[2-oxo-3-(prop-1-en-2-yl)-2,3-dihydro-1H-benzimidazol-1-yl]butanoateYield 104.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 19 g of 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one [described in J. Chem. Soc. Perkins, 1982, p. 261] in 150 ml of dimethylformamide was added with stirring at 20° C.±2° C. to 5.75 g of sodium hydride as a 50% suspension in oil and 10 ml of dimethylformamide and the mixture was stirred for another 30 minutes. 23.4 g of ethyl 4-bromo-butyrate were added to the mixture over 15 minutes and the mixture was stirred at room temperature for 4 hours and was poured into 800 ml of iced water. The mixture was extracted with ether and the organic phase was washed with water, dried and evaporated to dryness under reduced pressure to obtain 33 g of ethyl 2,3-dihydro-3-(1-methyl-ethenyl)-2-oxo-1H-benzimidazol-1-butanoate.

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. extractionThe mixture was extracted with ether
  3. washthe organic phase was washed with water
  4. customdried
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-acbea05ee6b34771bafea4f387426905
Source dataset
uspto-grants-1986_04
Patent number
US04585770

Reaction notes

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