4-Nitrobenzoic Acid → HCID 178423174, compound

HRID 1072543Notes

Reaction equation

HRID 1072543 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([CH3:9])[C:3]=1[NH2:10].[N+:11]([C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=O)=[CH:16][CH:15]=1)([O-:13])=[O:12]>O=P(Cl)(Cl)Cl>[N+:11]([C:14]1[CH:22]=[CH:21][C:17]([C:18]2[NH:10][C:3]3[C:4]([CH3:9])=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=3[N:1]=2)=[CH:16][CH:15]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 61084-Nitrobenzoic AcidHCID 5210773,4-Dimethylbenzene-1,2-diamine

Product 1

HCID 178423174HCID 178423174, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

2-(4-Nitrophenyl)-4,5-dimethyl benzimidazole was prepared by mixing 1,2-diamino-3,4-dimethylbenzene (1.36 g, 9.8 mmole) with 4-nitrobenzoic acid (1.67 g, 9.8 mmole) and dissolved in POCl3 (10 ml) and heated to reflux for 2.5 hours. The reaction mixture was cooled and cautiously poured onto ice. The resulting solid was filtered, washed with NaHCO3 and used without further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2.5 hours
  3. temperatureThe reaction mixture was cooled
  4. additioncautiously poured onto ice
  5. filtrationThe resulting solid was filtered
  6. washwashed with NaHCO3
  7. customused without further purification

Sources & evidence

ORD record
ord-2f0cba66e4b84d828866f30658b62367
Source dataset
uspto-grants-2005_06
Patent number
US06911462B2

Reaction notes

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