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

HRID 1984536Notes

Reaction equation

HRID 1984536 reaction equation
[CH3:1][N:2]([CH3:13])[CH2:3][CH2:4][NH:5][C:6]1[C:7]([NH2:12])=[CH:8][CH:9]=[CH:10][CH:11]=1.CN([CH:17]=[O:18])C>>[CH3:1][N:2]([CH3:13])[CH2:3][CH2:4][N:5]1[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:12][C:17]1=[O:18]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 522698N-[2-(dimethylamino)ethyl]benzene-1,2-diamine

Product 1

HCID 148946781-[2-(Dimethylamino)ethyl]-1,3-dihydrobenzimidazol-2-oneYield 85%

Procedure

A mixture of N-[2-(dimethylamino)ethyl]benzene-1,2-diamine (3.11 g, 17.3 mmol) and 1,1-carbonyldiimidazole (CDI) (3.2 g, 19 mmol) are heated in DMF to 110°-120° C. until reaction is complete by TLC, cooled and extracted with EtOAc. The combined extracts are washed with water, dried over MgSO4 and concentrated in vacuo. The resultant residue is purified by flash chromatography (silica gel, 94:5:1 CH2Cl2, methanol, concentrated NH4OH as eluent) to give the title compound as a dark purple solid, 3.03 g (85% yield), identified by HPLC and mass spectral analyses.

Workup

  1. temperaturecooled
  2. extractionextracted with EtOAc
  3. washThe combined extracts are washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue is purified by flash chromatography (silica gel, 94:5:1 CH2Cl2, methanol, concentrated NH4OH as eluent)

Sources & evidence

ORD record
ord-4b301474caa448018344cc56692b7d0a
Source dataset
uspto-grants-2009_06
Patent number
US07544701B2

Reaction notes

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