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

HRID 2267287Notes

Reaction equation

HRID 2267287 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].[OH2:19].Cl[CH2:21]Cl>>[O:19]=[C:21]1[N:8]([CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1]1

Participants

4

Reactant 3

HCID 962WaterHCID 6344DichloromethaneHCID 28875325tert-Butyl 2-[(2-Aminophenyl)amino]ethylcarbamate

Product 1

HCID 57428815tert-Butyl 2-(2-oxo-2,3-dihydrobenzo[d]imidazol-1-yl)ethylcarbamateYield 37%

Procedure

1,1-carbonyldiimidazole (0.36 g, 2.23 mmol) was added to a solution of tert-butyl 2-(2-aminophenylamino)ethylcarbamate (0.56 g, 2.23 mmol) in dichloromethane (15 mL) and stirred at rt overnight. Water (50 mL) was added and the mixture was extracted with dichloromethane (3×50 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate and filtered. The solvent was removed and the product was purified by column chromatography eluting with ethyl acetate/hexane (1:3) to give the title compound (230 mg, 37%).

Workup

  1. extractionthe mixture was extracted with dichloromethane (3×50 mL)
  2. washThe combined organic layers were washed with brine (50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed
  6. customthe product was purified by column chromatography
  7. washeluting with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-984c2defc52b4ca9b28cc96731fe7fb6
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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