Hydrochloric Acid → 1-Acetyl-6-methyl-3-(3-nitro-phenyl)pyrazolo[5,1-c][1,2,4]triazole

HRID 1742065Notes

Reaction equation

HRID 1742065 reaction equation
[C:1]([NH:4][C:5]1[N:9]([C:10](=[N:20]OS(C2C=CC(C)=CC=2)(=O)=O)[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[N:8]=[C:7]([CH3:32])[CH:6]=1)(=[O:3])[CH3:2].C1CCN2C(=NCCC2)CC1.Cl>CS(C)=O.O>[C:1]([N:4]1[C:5]2=[CH:6][C:7]([CH3:32])=[N:8][N:9]2[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)=[N:20]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 735084175-acetamido-3-methyl-1-(O-tosyl-3-nitro-benzohydroximoyl)-pyrazole

Product 1

HCID 190101071-Acetyl-6-methyl-3-(3-nitro-phenyl)pyrazolo[5,1-c][1,2,4]triazoleYield 90.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

800 mg (1.75 mmol) of 5-acetamido-3-methyl-1-(O-tosyl-3-nitro-benzohydroximoyl)-pyrazole are suspended in 10 ml of DMSO, treated with 0.8 ml DBU with stirring at room temperature, diluted with water and acidified with 2N hydrochloric acid. The precipitate obtained is filtered under suction, washed with water, a little methanol and a little ethyl acetate and recrystallised from methyl glycol. 450 mg (90%) of 1-acetyl-6-methyl-3-(3-nitro-phenyl)pyrazolo[5,1-c][1,2,4]triazole with a m. pt. of 207°-210° C. are obtained.

Workup

  1. customThe precipitate obtained
  2. filtrationis filtered under suction
  3. washwashed with water
  4. customa little methanol and a little ethyl acetate and recrystallised from methyl glycol

Sources & evidence

ORD record
ord-40c90b2901424f54aa045690bb3adc26
Source dataset
uspto-grants-1994_08
Patent number
US05336780

Reaction notes

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