Acetylacetone → N-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidin-2-yl)-2-nitrobenzenesulfonamide

HRID 980513Notes

Reaction equation

HRID 980513 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-:19])=[O:18])(=[O:10])=[O:9])[N:3]=1.[CH3:20][C:21](=O)[CH2:22][C:23](=O)[CH3:24]>C(O)(=O)C>[CH3:20][C:21]1[CH:22]=[C:23]([CH3:24])[N:6]2[N:5]=[C:4]([NH:7][S:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N+:17]([O-:19])=[O:18])(=[O:10])=[O:9])[N:3]=[C:2]2[N:1]=1

Participants

4

Reactant 2

HCID 31261AcetylacetoneHCID 13772880N-(5-Amino-1,2,4-triazol-3-yl)-2-nitrobenzenesulfonamide

Product 1

HCID 13772892N-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidin-2-yl)-2-nitrobenzenesulfonamideYield 82.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2.43 g (9.00 mmol) of N-(5-amino-1,2,4-triazol-3-yl)-2-nitrobenzenesulfonamide and 1.85 ml (1.80 g, 18.0 mmol) of 2,4 pentanedione in 25 ml of glacial acetic acid was heated at reflux for 19 hours. After cooling to room temperature, the solid which separated was collected by filtration, washed with acetic acid and dried in vacuo to yield 2.58 g (82 percent) of the desired product as an off-white crystalline solid, mp 255°-256° C. IR and 1H NMR spectra were in agreement with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 19 hours
  3. customthe solid which separated
  4. filtrationwas collected by filtration
  5. washwashed with acetic acid
  6. customdried in vacuo

Sources & evidence

ORD record
ord-47d6d18cde5d42caa5250388319fe600
Source dataset
uspto-grants-1987_01
Patent number
US04638075

Reaction notes

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