Triethylamine → 5-Amino-1-(3-nitro-benzohydroximoyl)-3-methyl-pyrazole

HRID 1742062Notes

Reaction equation

HRID 1742062 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([NH2:7])[CH:3]=1.C(N(CC)CC)C.[N+:15]([C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[C:21](Cl)=[N:22][OH:23])([O-:17])=[O:16]>O1CCOCC1>[NH2:7][C:4]1[N:5]([C:21](=[N:22][OH:23])[C:20]2[CH:25]=[CH:26][CH:27]=[C:18]([N+:15]([O-:17])=[O:16])[CH:19]=2)[N:6]=[C:2]([CH3:1])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 2756318alpha-Chloro-3-nitrobenzaldoxime

Product 1

HCID 735084165-Amino-1-(3-nitro-benzohydroximoyl)-3-methyl-pyrazoleYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4.85 g (0.05 mol) of 3(5)-amino-5(3)-methyl-pyrazole in 50 ml of absolute dioxan are treated with 8.3 ml (0,06 mol) of triethylamine and then, under stirring at room temperature, are treated dropwise with a solution of 10 g (0.05 mol) of 3-nitro-benzohydroximoyl chloride in 50 ml of absolute dioxan. Stirring is continued for 3 hours and then the mixture is evaporated to dryness. The residue is treated with water and ethyl acetate. The organic phase is dried over magnesium sulphate, evaporated under vacuum and the residue obtained in this way is recrystallised from dioxan. 9.8 g (48%) of 5-amino-1-(3-nitro-benzohydroximoyl)-3-methyl-pyrazole with a m. pt. of 224° to 226° C. are obtained.

Workup

  1. stirringStirring
  2. customthe mixture is evaporated to dryness
  3. additionThe residue is treated with water and ethyl acetate
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. customevaporated under vacuum
  6. customthe residue obtained in this way
  7. customis recrystallised from dioxan

Sources & evidence

ORD record
ord-9951e2f903c54e1da04e592485a75fc4
Source dataset
uspto-grants-1994_08
Patent number
US05336780

Reaction notes

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