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

HRID 365478Notes

Reaction equation

HRID 365478 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-e15bd21cb13f40588ad12984fbf713d4
Source dataset
uspto-grants-2000_10
Patent number
US06127395

Reaction notes

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