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

HRID 373052Notes

Reaction equation

HRID 373052 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 reaction mixture was refluxed for 16 hours and was concentrated under reduced pressure. The residue was diluted with chloroform and the insoluble matter was filtered off. The solvent was then 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 reaction mixture was refluxed for 16 hours
  2. concentrationwas concentrated under reduced pressure
  3. additionThe residue was diluted with chloroform
  4. filtrationthe insoluble matter was filtered off
  5. distillationThe solvent was then distilled off
  6. customthe residue was purified by silica gel chromatography (eluent:chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-4658f92cd19d4e258b38cb35967485a8
Source dataset
uspto-grants-1992_11
Patent number
US05162318

Reaction notes

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