Potassium Carbonate → HCID 9846654, compound

HRID 488735Notes

Reaction equation

HRID 488735 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C:7]2([NH:14][C:15]([NH:17][C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=3)=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2=O)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C:7]23[CH2:12][CH2:11][CH2:10][CH:9]=[C:8]2[N:17]([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=2)[C:15](=[O:16])[NH:14]3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 22268066HCID 22268066, compound

Product 1

HCID 9846654HCID 9846654, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A suspension of 1-[1-(4-bromo-benzyl)-2-oxocyclohexyl]-3-(3,5-dichlorophenyl)-urea (5.0 g) (0.0106 mol), K2CO3 (3.1 g) (2.1 eq) and molecular sieves 4A (15 g) in xylene (700 ml) was refluxed for 8 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 3a-(4-Bromo-benzyl)-1-(3,5-dichlorophenyl)-1,3,3a,4,5,6-hexahydro-benzimidazol-2-one (3.2 g) as a white solid. 1H NMR (CDCl3): 7.45 (2H, d), 7.20 (1H, m), 7.15 (2H, d), 7.05 (2H, m), 4.95 (1H, m), 3.0 (1H, d), 2.90 (1H, d), 2.5-2.1 (2H, m), 2.1-1.8 (3H, m), 1.8-1.6 (1H, m).

Workup

  1. temperaturewas refluxed for 8 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-cec3574c977a4856ae7d1ec42770bf80
Source dataset
uspto-grants-2005_12
Patent number
US06974815B2

Reaction notes

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