Nitric Acid → HCID 178526424, compound

HRID 17776Notes

Reaction equation

HRID 17776 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[NH:8][N:9]=[N:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[N+:13]([C:12]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]2[NH:10][N:9]=[N:8][C:7]=2[CH:11]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 178526497HCID 178526497, compound

Product 1

HCID 178526424HCID 178526424, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

5-Nitro-1H-benzotriazole was dissolved in conc. sulphuric acid (60 ml) and cooled to 0° C. in an ice bath. Nitric acid (60 ml, excess) was added drop wise to the cooled solution over a period of 20 minutes. Stirring was continued for another 15 minutes at 0° C. and then at 115° C. overnight, by which time TLC (A) indicated the conversion of starting material. The solution was cooled to room temperature and poured over ice to precipitate a pale yellow solid and a clear yellow solution. The solid was collected by filtration and washed with copious amounts of water until neutral to afford [19] in 67% yield. Rf (A) 0.34; δH(400 MHZ; DMSO-d6) 9.02 (2H, s, BT); m/z (FAB) 210.02695 [(M+H)+ calc. for C6H4N5O4 210.02633].

Workup

  1. customat 115° C.
  2. customovernight
  3. temperatureThe solution was cooled to room temperature
  4. additionpoured over ice
  5. customto precipitate a pale yellow solid
  6. filtrationThe solid was collected by filtration
  7. washwashed with copious amounts of water until neutral

Sources & evidence

ORD record
ord-5cf21c530e9342f0bc46c7e9da330753
Source dataset
uspto-grants-2010_06
Patent number
US07741102B2

Reaction notes

Loading…