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

HRID 916269

反応式

HRID 916269 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-5f26461ea2034018b59668be95f02de0
出典データセット
uspto-grants-2007_09
特許番号
US07268231B2

関連ノート

読み込み中…