4-Methyloxybenzyl chloride → HCID 178489494, compound

HRID 916270Notes

Reaction equation

HRID 916270 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.[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23](CCl)=[CH:22][CH:21]=1.[CH3:28]CN(C(C)C)C(C)C>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][CH2:28][C:27]1[CH:26]=[CH:23][CH:22]=[CH:21][C:20]=1[O:19][CH3:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 699934-Methyloxybenzyl chlorideHCID 81531DiisopropylethylamineHCID 150541832-Amino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester

Product 1

HCID 178489494HCID 178489494, compoundYield 42.5%

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), 4-methoxybenzylchloride (56.24 mg, 0.40 mmol) and Hunig's base (77.40 mg, 0.60 mmol) in acetonitrile (6 mL) was heated to reflux under argon for 13 hrs. 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-methoxyl-benzylamino)-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester as a white solid (60.0 mg, 42.5%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under argon for 13 hrs
  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-c3a6e54c925a4f73b5e8876f7b1972d8
Source dataset
uspto-grants-2007_09
Patent number
US07268231B2

Reaction notes

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