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

HRID 1631938Notes

Reaction equation

HRID 1631938 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][C:14]1[CH:19]=[C:18]([Cl:20])[C:17]([Cl:21])=[CH:16][C:15]=1[NH2:22].O>C1COCC1>[Cl:20][C:18]1[C:17]([Cl:21])=[CH:16][C:15]2[NH:22][C:1](=[O:2])[NH:13][C:14]=2[CH:19]=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-One

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.49 g (33.9 mmol) of 1,1′-carbonyldiimidazole were added in portions to a stirred solution of 5.00 g (28.2 mmol) of 1,2-diamino-4,5-dichlorobenzene in THF (100 ml) at room temperature. The reaction solution was then stirred at room temperature overnight. The reaction mixture was mixed with water (60 ml) and cooled in an ice bath. The precipitate which separated out was filtered, washed with water and dried in vacuo.

Workup

  1. temperaturecooled in an ice bath
  2. customThe precipitate which separated out
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-76aba82b504940e18d6be7e806e9f167
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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