O-Phenylenediamine → HCID 135696401, compound

HRID 725341Notes

Reaction equation

HRID 725341 reaction equation
[N+:1]([C:4]1[C:5]([OH:14])=[C:6]([O:12][CH3:13])[CH:7]=[C:8]([CH:11]=1)[CH:9]=O)([O-:3])=[O:2].[C:15]1([NH2:22])[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21].[N+](C1C=CC=CC=1)([O-])=O>CO>[N:21]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[NH:22][C:9]=1[C:8]1[CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]([OH:14])=[C:6]([O:12][CH3:13])[CH:7]=1

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 7416NitrobenzeneHCID 811345-Nitrovanillin

Product 1

HCID 135696401HCID 135696401, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

aa) A solution of 4.93 g of 5-nitrovanillin and 2.7 g of 1,2-phenylenediamine, in 45 ml of methanol and 15 ml of nitrobenzene is heated to boiling under reflux. After 15 minutes crystals begin to separate from the red solution. After 18 hours the reaction mixture is cooled to room temperature and diluted with 60 ml of methanol. The crystals are filtered under suction and washed with methanol. There is obtained 4-(2-benzimidazolyl)-2-methoxy-6-nitrophenol of m.p. 198°-200° (from N,N-dimethylformamide/methanol).

Workup

  1. temperatureunder reflux
  2. customto separate from the red solution
  3. additiondiluted with 60 ml of methanol
  4. filtrationThe crystals are filtered under suction
  5. washwashed with methanol

Sources & evidence

ORD record
ord-2c8e17cd62424670be8de54ece1afab3
Source dataset
uspto-grants-1998_01
Patent number
US05705703

Reaction notes

Loading…