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

HRID 1985812Notes

Reaction equation

HRID 1985812 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[CH:3]=1.[C:11](N1C=CN=C1)(N1C=CN=C1)=[O:12].O>O1CCCC1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]2[NH:9][C:11](=[O:12])[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 101.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4,5-Dichloro-1,2-phenylenediamine (10 g) was dissolved in tetrahydrofuran (35 mL), and to the mixture was added a suspension of carbonyldiimidazole (9.6 g) in tetrahydrofuran (15 mL) at room temperature. The reaction mixture was stirred at room temperature for 1 hour, and to the reaction mixture was added water under ice-cooling. The insoluble material was collected by filtration and dried to give the title compound (11.6 g).

Workup

  1. additionto the mixture was added
  2. temperaturecooling
  3. filtrationThe insoluble material was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-a20f4ca89b17436a9cd7d8df2b03fccb
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

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