Nitric Acid → HCID 178526738, compound

HRID 17778Notes

Reaction equation

HRID 17778 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]2[NH:6][N:7]=[N:8][C:4]=2[CH:3]=1.[N+:11]([O-])([OH:13])=[O:12]>S(=O)(=O)(O)O>[N+:11]([C:3]1[C:4]2[N:8]=[N:7][NH:6][C:5]=2[CH:9]=[CH:10][C:2]=1[Cl:1])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 178418767HCID 178418767, compound

Product 1

HCID 178526738HCID 178526738, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

5-Chloro-1H-benzotriazole (3.08 g, 20 mmol) was dissolved in conc. sulphuric acid (40 ml) and cooled to 0° C. on an ice bath. Nitric acid (40 ml, excess) was added drop wise to the cooled solution over a period of 20 minutes. Stirring was continued for 1 hour at 0° C. and then at 60° C. for an additional 1 hour, 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 white solid. The solid was collected by filtration and washed with copious amounts of water until neutral to afford [22] in 83% yield. Rf (A) 0.49 δH(400 MHz; DMSO-d6) 7.75 (1H, d, J8.8, BT) 8.38 (1H, br s, BT); m/z (EI−HR) 197.99383 [(M) calc. for C6H3N4O235Cl 197.99445] and 199.99345 [(M) calc. for C6H3N4O237Cl 199.99150].

Workup

  1. waitat 60° C. for an additional 1 hour
  2. temperatureThe solution was cooled to room temperature
  3. additionpoured over ice
  4. customto precipitate a white solid
  5. filtrationThe solid was collected by filtration
  6. washwashed with copious amounts of water until neutral

Sources & evidence

ORD record
ord-9640bdcdf36c4971b8fd9af98d635629
Source dataset
uspto-grants-2010_06
Patent number
US07741102B2

Reaction notes

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