4-Nitrobenzoic Acid → HCID 22387245, compound

HRID 1072540Notes

Reaction equation

HRID 1072540 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[NH2:12].[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=O)=[CH:18][CH:17]=1)([O-:15])=[O:14]>O=P(Cl)(Cl)Cl>[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20]2[NH:12][C:3]3[CH:4]=[C:5]([C:8]([F:9])([F:10])[F:11])[CH:6]=[CH:7][C:2]=3[N:1]=2)=[CH:18][CH:17]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 61084-Nitrobenzoic AcidHCID 5208224-Trifluoromethyl-1,2-phenylenediamine

Product 1

HCID 22387245HCID 22387245, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

2-(4-Nitrophenyl)-5-trifluoromethyl benzimidazole was synthesized as follows: 1,2-diamino-4-trifluoromethylbenzene (1.76 g, 10.0 mmole) was mixed with 4-nitrobenzoic acid (1.67 g, 9.8 mmole), dissolved in POCl3 (12 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-c5896fb5475e47178ac741f00242cc4f
Source dataset
uspto-grants-2005_06
Patent number
US06911462B2

Reaction notes

Loading…