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

HRID 488736노트

반응식

HRID 488736 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e9ba7d29de1d47e2b0a0db1fa83e4bcb
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06974815B2

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