3-Chloroaniline → 2H-Benzimidazol-2-one, 1,3-dihydro-6-chloro-1-(3-chlorophenyl)-

HRID 2258536Notes

Reaction equation

HRID 2258536 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-])=O.[Cl:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16].[C:20]([O-])(=[O:22])C.[Na+]>C(O)CO>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[NH:9][C:20](=[O:22])[N:16]([C:15]3[CH:17]=[CH:18][CH:19]=[C:13]([Cl:12])[CH:14]=3)[C:2]=2[CH:7]=1

Participants

5

Reactant 3

HCID 79323-ChloroanilineHCID 118992,4-DichloronitrobenzeneHCID 517045Sodium Acetate

Product 1

HCID 30618062H-Benzimidazol-2-one, 1,3-dihydro-6-chloro-1-(3-chlorophenyl)-

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of 50 g of 2,4-dichloro-1-nitrobenzene, 40 ml of 3-chloroaniline and 43 g of anhydrous sodium acetate in 220 ml of ethylene glycol is heated at reflux for 72 hours. After cooling, the precipitate formed is filtered off and washed with water. 39 g of the expected product are obtained after crystallization from iso ether, mp=112° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 72 hours
  3. temperatureAfter cooling
  4. customthe precipitate formed
  5. filtrationis filtered off
  6. washwashed with water

Sources & evidence

ORD record
ord-3c73c172d22741c494058f4cd544feab
Source dataset
uspto-grants-1997_08
Patent number
US05661169

Reaction notes

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