Nitric Acid → Benzimidazol-2-one

HRID 895760Notes

Reaction equation

HRID 895760 reaction equation
CC(C(N=NC1C=CC(Cl)=CC=1[N+]([O-])=O)C(N[C:8]1[CH:13]=[CH:12][C:11]2[NH:14][C:15]([NH:17][C:10]=2[CH:9]=1)=[O:16])=O)=O.[Br-].NC1C=C[N+](CC)=CC=1.[N+]([O-])(O)=O.N([O-])=O.[Na+]>O>[N:14]1[C:15](=[O:16])[N:17]=[C:10]2[CH:9]=[CH:8][CH:13]=[CH:12][C:11]=12

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 25535C.I. Pigment OrangeHCID 13073421p-Amino-n-ethylpyridinium bromideHCID 23668193Sodium Nitrite

Product 1

HCID 162542Benzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

20 parts of abenzimidazolone orange pigment (C.I. pigment orange 36) which had been previously finely ground and 62 parts of p-amino-N-ethylpyridinium bromide were dispersed in 150 parts of water. To the mixture were then added dropwise 32 parts of nitric acid. The mixture was then stirred at a temperature of 75° C. for 5 minutes. To the mixture was then added an aqueous solution of sodium nitrite. The mixture was further stirred for 2 hours, and then repeatedly rinsed and filtered to obtain a slurry of a surface-treated benzimidazolone orange pigment having an N-ethylpyridyl group introduced therein with the interposition of phenyl group.

Workup

  1. stirringThe mixture was further stirred for 2 hours
  2. washrepeatedly rinsed
  3. filtrationfiltered

Sources & evidence

ORD record
ord-0585871de8ee4d9eb9d87c52fda35eca
Source dataset
uspto-grants-2005_07
Patent number
US06916862B2

Reaction notes

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