Sodium → 1-[2-(Dimethylamino)ethyl]-1,3-dihydrobenzimidazol-2-one

HRID 373068Notes

Reaction equation

HRID 373068 reaction equation
[Na].C(OC([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]([C:20]([O:22]CC)=O)[CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])=O)C>C(O)C>[CH3:18][N:17]([CH3:19])[CH2:16][CH2:15][N:14]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:20]1=[O:22]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 19811379N-(2-ethoxycarbonylaminophenyl)-N-ethoxycarbonyl-N',N'-dimethylethylenediamine

Product 1

HCID 148946781-[2-(Dimethylamino)ethyl]-1,3-dihydrobenzimidazol-2-oneYield 86.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In ethanol (100 ml) was dissolved sodium metal (0.70 g) followed by addition of a solution of N-(2-ethoxycarbonylaminophenyl)-N-ethoxycarbonyl-N',N'-dimethylethylenediamine (4.88 g) in ethanol (20 ml). The mixture was refluxed overnight and the solvent was then distilled off under reduced pressure. To the residue was added chloroform and the insoluble matter was filtered off. The solvent was distilled off and the residue was purified by silica gel chromatography (eluent: chloroform:methanol=10:1) to give 2.69 g of 1,3-dihydro-1-(2-dimethylaminoethyl)-2H-benzimidazol-2-one.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. distillationthe solvent was then distilled off under reduced pressure
  3. additionTo the residue was added chloroform
  4. filtrationthe insoluble matter was filtered off
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by silica gel chromatography (eluent: chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-999b71d1f4fa4402b42caec6c101dd0a
Source dataset
uspto-grants-1992_11
Patent number
US05162318

Reaction notes

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