4,5-Dichloro-1,2-phenylenediamine → 5,6-Dichloro-2-(4-methoxy-3-nitro-phenyl)-1h-benzoimidazole

HRID 25497

Reaction equation

HRID 25497 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].S(=O)(O)[O-].[Na+].[Cl:19][C:20]1[CH:25]=[C:24]([NH2:26])[C:23]([NH2:27])=[CH:22][C:21]=1[Cl:28]>C(O)C>[Cl:19][C:20]1[C:21]([Cl:28])=[CH:22][C:23]2[NH:27][C:7]([C:6]3[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[C:4]([N+:11]([O-:13])=[O:12])[CH:5]=3)=[N:26][C:24]=2[CH:25]=1

Participants

5

Reactant 3

HCID 792974,5-Dichloro-1,2-phenylenediamineHCID 7006084-Methoxy-3-nitrobenzaldehydeHCID 23665763Sodium Bisulfite

Product 1

HCID 225684155,6-Dichloro-2-(4-methoxy-3-nitro-phenyl)-1h-benzoimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Methoxy-3-nitrobenzaldehyde (4.65 g, 27.6 mmol) and sodium bisulfite (5.79 g, 55.2 mmol) were added to ethanol (200 mL) and refluxed for 4 hours at which time 1,2-dichloro-4,5-phenylenediamine (4.56 g, 27.6 mmol) was added and the mixture was refluxed overnight. The reaction mixture was filtered while hot, and the pea-green solid washed with ethanol.(3.09 g) mp 250° C.

Workup

  1. additionwas added
  2. temperaturethe mixture was refluxed overnight
  3. filtrationThe reaction mixture was filtered while hot, and the pea-green solid
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-097d8dbdd5a44471b9b185e4e9e2f18d
Source dataset
uspto-grants-2005_02
Patent number
US06858739B2

Linked notes

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