Cyclohexanone, 2-hydroxy- → 2-phenyl-4,5,6,7-tetrahydro-1H-benzimidazole

HRID 727455

Reaction equation

HRID 727455 reaction equation
Cl.[C:2]([NH2:10])(=[NH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O[CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13]1=O>[OH-].[NH4+]>[C:3]1([C:2]2[NH:9][C:12]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 10785Cyclohexanone, 2-hydroxy-HCID 80289Benzamidine, hydrochloride

Product 1

HCID 38522962-phenyl-4,5,6,7-tetrahydro-1H-benzimidazoleYield 37.6%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 6.3 g benzamidine hydrochloride in 60 mL ammonium hydroxide was added 4.6 g 2-hydroxycyclohexanone. The reaction mixture was heated to 90° C. for 7 hours in a sealed tube. On cooling to room temperature the crystals formed were collected by filtration and after drying yielded 3.0 g 2-phenyl-4,5,6,7,-tetrahydrobenzimidazole (Compound 136), m.p. 300°-301° C.

Workup

  1. temperatureOn cooling to room temperature the crystals
  2. customformed
  3. filtrationwere collected by filtration
  4. customafter drying

Sources & evidence

ORD record
ord-207d847bb60146a59b8aed75e53df056
Source dataset
uspto-grants-1998_01
Patent number
US05712392

Linked notes

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