Sulfuryl chloride → 3-Amino-4-chloro-1-methyl-5-trifluoromethylpyrazole

HRID 743682Notes

Reaction equation

HRID 743682 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([F:10])([F:9])[F:8])[N:4]([CH3:11])[N:3]=1.S(Cl)([Cl:15])(=O)=O.C(=O)([O-])O.[Na+]>C(#N)C>[NH2:1][C:2]1[C:6]([Cl:15])=[C:5]([C:7]([F:8])([F:10])[F:9])[N:4]([CH3:11])[N:3]=1

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 229127981-Methyl-5-(trifluoromethyl)-1H-pyrazol-3-amine

Product 1

HCID 229128013-Amino-4-chloro-1-methyl-5-trifluoromethylpyrazoleYield 92.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.0 g (12.1 mmole) 3-Amino-1-methyl-5-trifluoromethylpyrazole in 20 ml acetonitrile was treated with 1.8 g (13.3 mmole) sulfuryl chloride and the mixture stirred for 2 hours at room temperature. It was poured into aqueous saturated sodium hydrogen carbonate, extracted with ethyl acetate, dried over sodium sulfate and concentrated. 2.24 g 3-Amino-4-chloro-1-methyl-5-trifluoromethylpyrazole was obtained, which was treated without further purification as described under 2 (Example 1) to give 4-chloro-3-hydrazino-1-methyl-5-trifluoromethylpyrazole.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-80cfa857dce04a8fb44d7f0be9a65d80
Source dataset
uspto-grants-1996_09
Patent number
US05556986

Reaction notes

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