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

HRID 488736Notes

Reaction equation

HRID 488736 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-e9ba7d29de1d47e2b0a0db1fa83e4bcb
Source dataset
uspto-grants-2005_12
Patent number
US06974815B2

Reaction notes

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