Dimethylformamide → tert-Butyl 2-(2-oxo-2,3-dihydrobenzo[d]imidazol-1-yl)ethylcarbamate

HRID 1984539Notes

Reaction equation

HRID 1984539 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][CH2:9][NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH2:17])([CH3:4])([CH3:3])[CH3:2].CN([CH:22]=[O:23])C>>[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][CH2:9][N:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH:17][C:22]1=[O:23])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 28875325tert-Butyl 2-[(2-Aminophenyl)amino]ethylcarbamate

Product 1

HCID 57428815tert-Butyl 2-(2-oxo-2,3-dihydrobenzo[d]imidazol-1-yl)ethylcarbamateYield 56%

Procedure

A mixture of [2-(2-aminophenylamino)ethyl]carbamic acid t-butyl ester (3.85 g, 15.3 mmol) and 1,1-carbonyldiimidazole (CDI) (2.73 g, 16.8 mmol) in DMF are heated at 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, 1:1 CH2Cl2: EtOAc as eluent) to give the title compound as a brown solid, 2.4 g (56% yield), identified by HPLC and mass spectral analyses.

Workup

  1. temperatureare heated at 110°-120° C. until reaction
  2. temperaturecooled
  3. extractionextracted with EtOAc
  4. washThe combined extracts are washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue is purified by flash chromatography (silica gel, 1:1 CH2Cl2: EtOAc as eluent)

Sources & evidence

ORD record
ord-bf748a7269644748aa61c978748324c5
Source dataset
uspto-grants-2009_06
Patent number
US07544701B2

Reaction notes

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