O-Phenylenediamine → HCID 135696401, compound

HRID 2260243Notes

Reaction equation

HRID 2260243 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]>CO.[N+](C1C=CC=CC=1)([O-])=O>[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 2

HCID 7243O-PhenylenediamineHCID 811345-Nitrovanillin

Product 1

HCID 135696401HCID 135696401, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7416NitrobenzeneSolvent

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-0e13351331a443d39d59f50ececf17f9
Source dataset
uspto-grants-1995_12
Patent number
US05476875

Reaction notes

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