Triethylamine → 4-(4-Diazo-3-methyl-5-oxo-2-pyrazolin-1-yl)benzoic acid

HRID 1266960Notes

Reaction equation

HRID 1266960 reaction equation
[CH3:1][C:2]1[CH2:6][C:5](=[O:7])[N:4]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[N:3]=1.C1(C)C=CC(S([N:26]=[N+:27]=[N-])(=O)=O)=CC=1.C(N(CC)CC)C>CO>[N+:26](=[C:6]1[C:5](=[O:7])[N:4]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[N:3]=[C:2]1[CH3:1])=[N-:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13661p-Toluenesulfonyl azideHCID 1090294-(3-Methyl-5-oxo-2-pyrazolin-1-yl)benzoic acid

Product 1

HCID 1355026194-(4-Diazo-3-methyl-5-oxo-2-pyrazolin-1-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(3-methyl-5-oxo-2-pyrazolin-1-yl)benzoic acid (5.0 g, 0.023 mol) and p-toluenesulfonylazide (5.03 g, 0.026 mol) in methanol (30.0 mL) was treated with triethylamine (5.2 g; 0.051 mol.) and the reaction was stirred at room temperature for 5 hours.

Sources & evidence

ORD record
ord-e4ac385ef28a413c8cc30c3437ac2ecb
Source dataset
uspto-grants-2003_04
Patent number
US06552008B1

Reaction notes

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