Potassium Carbonate → 4-[1-(3,5-Dichlorophenyl)-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile

HRID 488736ノート

反応式

HRID 488736 の反応式
[C:1]([C:3]1[CH:28]=[CH:27][C:6]([CH2:7][C:8]2([NH:15][C:16]([NH:18][C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=3)=[O:17])[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=O)=[CH:5][CH:4]=1)#[N:2].C([O-])([O-])=O.[K+].[K+]>C1(C)C(C)=CC=CC=1>[Cl:26][C:21]1[CH:20]=[C:19]([N:18]2[C:9]3=[CH:10][CH2:11][CH2:12][CH2:13][C:8]3([CH2:7][C:6]3[CH:27]=[CH:28][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[NH:15][C:16]2=[O:17])[CH:24]=[C:23]([Cl:25])[CH:22]=1

参加物

4

反応物 2

HCID 11430Potassium CarbonateHCID 222680621-[1-(4-Cyano-benzyl)-2-oxocyclohexyl]-3-(3,5-dichlorophenyl)-urea

生成物 1

HCID 104534514-[1-(3,5-Dichlorophenyl)-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile収率 50.2%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

A suspension of 1-[1-(4-cyano-benzyl)-2-oxocyclohexyl]-3-(3,5-dichlorophenyl)-urea (3.7 g) (0.009 mol), K2CO3 (2.6 g) (2.1 eq) and molecular sieves 4A (10 g) in xylene (500 ml) was refluxed 16 h. After cooling, the reaction mixture was filtered on paper, concentrated in vacuo, and the residue purified on SiO2 chromatography (eluent EtOAc/cyclohexane-3/7) to yield 4-[1-(3,5-Dichlorophenyl)-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile (1.8 g) as a white solid. 1H NMR (CDCl3): 7.6 (2H, d), 7.35 (2H, d), 7.15 (1H, m), 6.95 (2H, m), 5.65 (1H, bs), 4.95 (1H, m), 3.1 (1H, d), 2.9 (1H, d), 2.5-2.1 (2H, m), 2.1-1.65 (4H, m).

後処理

  1. temperaturewas refluxed 16 h
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered on paper
  4. concentrationconcentrated in vacuo
  5. customthe residue purified on SiO2 chromatography (eluent EtOAc/cyclohexane-3/7)

出典と根拠

ORDレコード
ord-e9ba7d29de1d47e2b0a0db1fa83e4bcb
出典データセット
uspto-grants-2005_12
特許番号
US06974815B2

反応ノート

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