Urea → 2H-Benzimidazol-2-one, 5-chloro-1,3-dihydro-1-(1-methylethyl)-

HRID 1654476Notes

Reaction equation

HRID 1654476 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[NH:4][CH:5]([CH3:7])[CH3:6].N[C:14](N)=[O:15]>O>[Cl:12][C:10]1[CH:9]=[CH:8][C:3]2[N:4]([CH:5]([CH3:7])[CH3:6])[C:14](=[O:15])[NH:1][C:2]=2[CH:11]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 27357454-Chloro-N~1~-(propan-2-yl)benzene-1,2-diamine

Product 1

HCID 108461602H-Benzimidazol-2-one, 5-chloro-1,3-dihydro-1-(1-methylethyl)-Yield 43.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2-amino-4-chloro-N-isopropylaniline (14 g) and urea (15 g) was stirred at 160° C. for 3.5 hours. After cooling, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with diluted hydrochloric acid, an aqueous sodium hydroxide solution, a saturated sodium chloride solution and dried over anhydrous magnesium sulfate and then the solvent was distilled off under reduced pressure. To the residue was added isopropyl alcohol and the obtained crystal was separated by filtration and recrystallized from acetonitrile to give 5-chloro-1-isopropylbenzimidazol-2-one (7 g).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with diluted hydrochloric acid
  4. dry with materialan aqueous sodium hydroxide solution, a saturated sodium chloride solution and dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionTo the residue was added isopropyl alcohol
  7. customthe obtained crystal was separated by filtration
  8. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-0ffd5348313c483d8daac2673a2bbd66
Source dataset
uspto-grants-1995_04
Patent number
US05407936

Reaction notes

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