4-Toluenesulfonyl chloride → 5-amino-3-methyl-1-(O-tosyl-3-nitrobenzohydroximoyl)-pyrazole

HRID 1742063Notes

Reaction equation

HRID 1742063 reaction equation
[NH2:1][C:2]1[N:6]([C:7](=[N:17][OH:18])[C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=2)[N:5]=[C:4]([CH3:19])[CH:3]=1.C(N(CC)CC)C.[CH3:27][C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1>C(#N)C>[NH2:1][C:2]1[N:6]([C:7](=[N:17][O:18][S:34]([C:31]2[CH:32]=[CH:33][C:28]([CH3:27])=[CH:29][CH:30]=2)(=[O:36])=[O:35])[C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=2)[N:5]=[C:4]([CH3:19])[CH:3]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 735084165-Amino-1-(3-nitro-benzohydroximoyl)-3-methyl-pyrazole

Product 1

HCID 735084195-amino-3-methyl-1-(O-tosyl-3-nitrobenzohydroximoyl)-pyrazoleYield 73.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

7.4 g (0.028 mol) of 5-amino-1-(3-nitro-benzohydroximoyl)-3-methyl-pyrazole are treated in 90 ml of absolute acetonitrile with 4 ml (0.028 mol) of triethylamine and then, with stirring at room temperature, are treated dropwise with a solution of 5.55 g (0.029 mol) of 4-tosyl chloride in 150 ml of absolute acetonitrile. Stirring is continued for 1 hour and then the mixture is evaporated to dryness. The residue is treated with water and ethyl acetate, the organic phase is washed with water, dried over magnesium sulphate and evaporated under vacuum. The oily residue obtained in this way is crystallised from ethanol. 8.5 g (72%) of 5-amino-3-methyl-1-(O-tosyl-3-nitrobenzohydroximoyl)-pyrazole with a m. pt. of 156°-158° C. are obtained. The substance is light-sensitive. On recrystallising twice from ethanol, the m. pt. is 165°-169° C.

Workup

  1. stirringStirring
  2. customthe mixture is evaporated to dryness
  3. additionThe residue is treated with water and ethyl acetate
  4. washthe organic phase is washed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated under vacuum
  7. customThe oily residue obtained in this way
  8. customis crystallised from ethanol

Sources & evidence

ORD record
ord-9e7aea21da4748b6b736179a167e9b9f
Source dataset
uspto-grants-1994_08
Patent number
US05336780

Reaction notes

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