Acetic Acid → 4,5,6,7-Tetrahydro-2-benzimidazolone

HRID 1683352Notes

Reaction equation

HRID 1683352 reaction equation
Br[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.[NH2:9][C:10]([NH2:12])=[O:11].C([O-])(=O)C.[NH4+].C(O)(=O)C>O>[N:9]1[C:10](=[O:11])[N:12]=[C:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=12

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1176UreaHCID 517165Ammonium AcetateHCID 117897582-Bromocyclohexanone

Product 1

HCID 232922894,5,6,7-Tetrahydro-2-benzimidazolone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-bromocyclohexanone (6.23 g, 0.035 mol) and urea (2.1 g, 0.035 mol) is refluxed in a solution of ammonium acetate (10 g), acetic acid (15 mL) and water (50 mL) for 4 h. Upon cooling slowly to room temp, white crystals form in the reaction vessel. The solid is collected by suction filtration, washed thoroughly with water and ether, and dried in vacuo to afford 4,5,6,7-tetrahydro-2-benzimidazolone (Compound 7).

Workup

  1. filtrationThe solid is collected by suction filtration
  2. washwashed thoroughly with water and ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-4314b798c9844be48a37a26ffe395954
Source dataset
uspto-grants-1997_06
Patent number
US05637725

Reaction notes

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