Dichloromethane → ethyl 5-chloro-2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylate

HRID 1062437ノート

反応式

HRID 1062437 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:12]=1.C(Cl)[Cl:26]>O>[Cl:26][C:10]1[N:9]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[N:12][C:11]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

参加物

4

反応物 2

HCID 6344DichloromethaneHCID 22285380HCID 22285380、化合物

生成物 1

HCID 22285463ethyl 5-chloro-2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylate収率 20%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a solution of ethyl 2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylate (270 mg, 0.75 mmol) in CH2Cl2 (5 mL) was added SO2Cl2 (1.6 mL, 20 mmol). The mixture was heated at reflux overnight, and diluted with water. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography over silica gel (33% EtOAc in hexane) to give ethyl 5-chloro-2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylate (60 mg) in 20% yield as a white solid: LC-MS m/z 395.0 (MH+), retention time 3.45 min (method 1). This intermediate, which is an example of Formula X in Scheme 2, was converted into 5-chloro-2-(2-chlorophenyl)-1-(4-chlorophenyl)-N-(1-piperidinyl)-1H-imidazole-4-carboxamide (Table entry 21).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography over silica gel (33% EtOAc in hexane)

出典と根拠

ORDレコード
ord-c8897cf4fef4447c8026ab844bde80f8
出典データセット
uspto-grants-2005_11
特許番号
US06960601B2

反応ノート

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