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

HRID 919357

Reaction equation

HRID 919357 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH2:9])=[CH:6][C:7]=1[Cl:8].C1N=CN([C:16](N2C=NC=C2)=[O:17])C=1.O>CN(C=O)C>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]2[NH:9][C:16](=[O:17])[NH:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 792974,5-Dichloro-1,2-phenylenediamine

Product 1

HCID 98991485,6-Dichloro-1,3-Dihydro-2H-Benzimidazol-2-OneYield 91.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of 4,5-dichloro-benzene-1,2-diamine (25 g, 0.14 mol) in dry DMF (200 mL), was added CDI (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-d736183869774be2acd93ff99c6c46df
Source dataset
uspto-grants-2016_03
Patent number
US09273034B2

Linked notes

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