Nitric Acid → 5-Chloro-1,3-dimethyl-4-nitro-1H-pyrazole

HRID 1678846Notes

Reaction equation

HRID 1678846 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[CH:3]=1.S(=O)(=O)(O)O.[N+:14]([O-])([OH:16])=[O:15]>>[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[N+:14]([O-:16])=[O:15]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 5215075-Chloro-1,3-dimethylpyrazole

Product 1

HCID 2795155-Chloro-1,3-dimethyl-4-nitro-1H-pyrazole

Procedure

148.0 gms. of 5-chloro-1,3-dimethylpyrazole are added to 530 ml. of concentrated sulfuric acid at 0° and 370 ml. of fuming nitric acid are added dropwise with stirring. The reaction mixture is then stirred at 0° for 4 hours, poured over 250 gms. of ice and extracted with methylene chloride. 138 gms. of the product, 5-chloro-1,3-dimethyl-4-nitro-1H-pyrazole, are obtained from the dried organic phase as white crystals, m.p. 77°-78°.

Workup

  1. customat 0°
  2. stirringThe reaction mixture is then stirred at 0° for 4 hours
  3. additionpoured over 250 gms
  4. extractionof ice and extracted with methylene chloride

Sources & evidence

ORD record
ord-1a85980e4b4a49f0bafc142f0ccae478
Source dataset
uspto-grants-1978_03
Patent number
US04077956

Reaction notes

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