o-Xylyl bromide → HCID 178424257, compound

HRID 916268Notes

Reaction equation

HRID 916268 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14](=[O:16])[N:13]=[C:12]1[NH2:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:19][C:20]1[C:21]([CH3:26])=[CH:22][CH:23]=[CH:24][CH:25]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14](=[O:16])[N:13]=[C:12]1[NH:17][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6992o-Xylyl bromideHCID 11430Potassium CarbonateHCID 150541832-Amino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester

Product 1

HCID 178424257HCID 178424257, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 2-amino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester (93.2 mg, 0.40 mmol), alpha-bromo-o-xylene (74.02 mg, 0.40 mmol) and K2CO3 (166.0 mg, 1.20 mmol) in acetonitrile (10 mL) was heated to reflux under argon for 1 hr. Cool to r.t., the reaction mixture was partitioned between EtOAc and water. The organic layer was dried over Na2SO4 and concentrated to give an oil which was purified by preparative TLC, eluted with 50% nHex/EtOAc to give 2-(2-methyl-benzylamino)-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester as a white solid (58.0 mg, 42.9%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under argon for 1 hr
  3. customthe reaction mixture was partitioned between EtOAc and water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customto give an oil which
  7. customwas purified by preparative TLC
  8. washeluted with 50% nHex/EtOAc

Sources & evidence

ORD record
ord-94fbfb3cfa4f43f0926dbd900bf5171d
Source dataset
uspto-grants-2007_09
Patent number
US07268231B2

Reaction notes

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