Nitric Acid → HCID 178423513, compound

HRID 17779Notes

Reaction equation

HRID 17779 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[CH:14]=[CH:13][C:9]2[NH:10][N:11]=[N:12][C:8]=2[CH:7]=1>S(=O)(=O)(O)O>[N+:1]([C:7]1[C:8]2[N:12]=[N:11][NH:10][C:9]=2[CH:13]=[CH:14][C:6]=1[CH3:5])([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 178423511HCID 178423511, compound

Product 1

HCID 178423513HCID 178423513, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Nitric acid (40 ml, excess) was added drop wise over 20 minutes to a stirred solution of 5-methyl-1H-benzotriazole (2.66 g, 20 mmol) in conc. sulphuric acid (40 ml) at 0° C. Stirring was continued at room temperature for 90 minutes by which time TLC (A) indicated complete reaction. The solution was poured onto ice to precipitate a flocculent white solid. The solid was collected by filtration and washed with water to afford [23] in 94% yield. Rf (A) 0.60 δH(400 MHz; DMSO-d6) 2.79 (3H, s, CH3) 7.52 (1H, d, J8.4, BT) 8.36 (1H, br s, BT) 16.26 (1H, s, NH); m/z (EI−HR) 178.04937 [(M) calc. for C7H6N4O2 178.04908].

Workup

  1. customreaction
  2. additionThe solution was poured onto ice
  3. customto precipitate a flocculent white solid
  4. filtrationThe solid was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-855c5b9a441c4513815442d70214d253
Source dataset
uspto-grants-2010_06
Patent number
US07741102B2

Reaction notes

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