Water → 5,6-Dichloro-1,3-Dihydro-2H-Benzimidazol-2-One

HRID 408674

Reaction equation

HRID 408674 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH2:9])=[CH:6][C:7]=1[Cl:8].O.CN([CH:15]=[O:16])C>>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]2[NH:9][C:15](=[O:16])[NH:10][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 792974,5-Dichloro-1,2-phenylenediamine

Product 1

HCID 98991485,6-Dichloro-1,3-Dihydro-2H-Benzimidazol-2-OneYield 90%

Procedure

To the solution of 4,5-dichloro-benzene-1,2-diamine (25 g, 0.14 mol) in dry DMF (200 mL), was added CU (23 g, 0.14 mol) as the solid. The reaction solution was stirred at room temperature for 1 hour, then water (500 mL) was added. The precipitated solid was collected by filtration, washed with water, dried thoroughly to afford the titled compound (26.0 g, 90%). The crude product was used in the following reaction without further purification.

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with water
  3. customdried thoroughly

Sources & evidence

ORD record
ord-32e380d95b384ff68651510f7cc8c2b2
Source dataset
uspto-grants-2014_06
Patent number
US08759345B2

Linked notes

Loading…