Potassium Carbonate → benzyl 2-[(2,4-dimethylphenyl)methylamino]-5-oxo-4H-imidazole-3-carboxylate

HRID 916269

반응식

HRID 916269 반응식
[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][C:19]1[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:20]=1[CH2:21]Br.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][CH2:21][C:20]1[CH:23]=[CH:24][C:25]([CH3:27])=[CH:26][C:19]=1[CH3:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 27346041-(Bromomethyl)-2,4-dimethylbenzeneHCID 150541832-Amino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester

생성물 1

HCID 178425527benzyl 2-[(2,4-dimethylphenyl)methylamino]-5-oxo-4H-imidazole-3-carboxylate수율 24.9%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A suspension of 2-amino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester (93.2 mg, 0.40 mmol), 2,4-dimethylbenzylbromide (79.64 mg, 0.40 mmol) and K2CO3 (83.01 mg, 0.60 mmol) in acetonitrile (8 mL) was heated to reflux under argon for 45 min. Partition between EtOAc and water to give a suspension. Filter off the solid to give 2-(2,4-dimethyl-benzylamino)-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester (35.0 mg). The filtrate was separated, dried to give an oil which was purified by preparative TLC, eluted with 50% nHex/EtOAc to give 60.0 mg of 2-(2, 4-dimethyl-benzylamino)-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester as a white solid (total yield: 95.0 mg, 67.7%).

후처리

  1. temperaturewas heated
  2. temperatureto reflux under argon for 45 min
  3. customPartition between EtOAc and water
  4. customto give a suspension
  5. filtrationFilter off the solid

출처 및 근거

ORD 기록
ord-5f26461ea2034018b59668be95f02de0
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268231B2

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