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

HRID 36867Notes

Reaction equation

HRID 36867 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:12])[C:5]([NH2:11])=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].N[C:14](N)=[O:15]>>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]2[NH:11][C:14](=[O:15])[NH:12][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 1176UreaHCID 57026184-Chloro-5-nitro-o-phenylenediamine

Product 1

HCID 145662265-Chloro-1,3-dihydro-6-nitro-2H-benzimidazol-2-one

Procedure

A mixture of 14 g (0.074 mol) of 4-chloro-5-nitro-1,2-benzenediamine and of 13.44 g (0.226 mol) of urea is heated at 180° C. for 4 hours. The reaction mixture is cooled and evaporated to dryness. The residue is taken up in methanol and evaporated again. The residue is triturated in ether and a solid is obtained which is filtered. The product is used as is in the subsequent stages.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customevaporated to dryness
  3. customevaporated again
  4. customThe residue is triturated in ether
  5. customa solid is obtained which
  6. filtrationis filtered

Sources & evidence

ORD record
ord-48938a94b76547d78882f6917891a754
Source dataset
uspto-grants-1995_05
Patent number
US05418241

Reaction notes

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