Ethylene Oxide → 1,3-dihydro-1-(2-hydroxyethyl)-5-methyl-3-(1-methylethenyl)-2H-benzimidazol-2-one

HRID 258832Notes

Reaction equation

HRID 258832 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([C:11]([CH3:13])=[CH2:12])[C:6]=2[CH:14]=1.C[O-].[Na+].[O:18]1[CH2:20][CH2:19]1>C(O)C>[OH:18][CH2:19][CH2:20][N:9]1[C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:14][C:6]=2[N:7]([C:11]([CH3:13])=[CH2:12])[C:8]1=[O:10]

Participants

5

Reactant 3

HCID 6354Ethylene OxideHCID 4184312HCID 4184312, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 214248201,3-dihydro-1-(2-hydroxyethyl)-5-methyl-3-(1-methylethenyl)-2H-benzimidazol-2-oneYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred mixture of 37.6 parts of 1,3-dihydro-6-methyl-1-(1-methylethenyl)-2H-benzimidazol-2-one, 2 parts of sodium methoxide solution 30% and 320 parts of absolute ethanol is added a solution of 22 parts of oxirane in 40 parts of absolute ethanol. Stirring is continued first overnight at room temperature and further for 3 hours at reflux. The ethanol is evaporated, yielding 46 parts (100%) of 1,3-dihydro-1-(2-hydroxyethyl)-5-methyl-3-(1-methylethenyl)-2H-benzimidazol-2-one as an oily residue.

Workup

  1. temperatureat reflux
  2. customThe ethanol is evaporated

Sources & evidence

ORD record
ord-4ae5ce4a5b924a19a451062b576a7585
Source dataset
uspto-grants-1977_07
Patent number
US04035369

Reaction notes

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