1,1'-Carbonyldiimidazole → 5-Chloro-1,3-dihydro-6-nitro-2H-benzimidazol-2-one

HRID 2401488Notes

Reaction equation

HRID 2401488 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([NH2:11])=[C:4]([NH2:12])[CH:3]=1.C1N=CN([C:18](N2C=NC=C2)=[O:19])C=1>C1COCC1>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]2[NH:11][C:18](=[O:19])[NH:12][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 57026184-Chloro-5-nitro-o-phenylenediamine

Product 1

HCID 145662265-Chloro-1,3-dihydro-6-nitro-2H-benzimidazol-2-oneYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 4-chloro-5-nitro-1,2-phenylenediamine (2.0 g, 10.66 mmol) and CDI (2.59 g, 16 mmol) in anhydrous THF (50 mL) was heated to 85° C. for 4 h. The reaction was allowed to cool and the solvents were removed under reduced pressure. The resulting residue was washed with 2M aqueous hydrochloric acid and recrystallised from methanol to afford 5-chloro-6-nitro-1H-benzo[d]imidazol-2(3H)-one as a brown solid (1.9 g, 84%), which was taken through to the next step with no further purification.

Workup

  1. temperatureto cool
  2. customthe solvents were removed under reduced pressure
  3. washThe resulting residue was washed with 2M aqueous hydrochloric acid
  4. customrecrystallised from methanol

Sources & evidence

ORD record
ord-e68b6d7080e049eaa3e7dcf43a4664da
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

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