Sodium Hydroxide → 3-Hydrazino-1-methyl-5-trifluoromethylpyrazole

HRID 1653947Notes

Reaction equation

HRID 1653947 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.[N:12]([O-])=O.[Na+].[Sn](Cl)(Cl)(Cl)Cl.[OH-].[Na+]>Cl.O>[NH:1]([C:2]1[CH:6]=[C:5]([C:7]([F:8])([F:10])[F:9])[N:4]([CH3:11])[N:3]=1)[NH2:12]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 229127981-Methyl-5-(trifluoromethyl)-1H-pyrazol-3-amineHCID 23668193Sodium Nitrite

Product 1

HCID 229128033-Hydrazino-1-methyl-5-trifluoromethylpyrazoleYield 77.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 1.0 g (6.06 mmole) 3-amino-1-methyl-5-trifluoromethylpyrazole in 15 ml 6N hydrochloric acid, 0.52 g (7.44 mmole) sodium nitrite in 2 ml water was added slowly dropwise at 5° C. The mixture was stirred for 1.5 hours at the same temperature. Then 3.35 g (14.85 mmole) tin chloride (SnCl2.2H2O) in 3 ml concentrated hydrochloric acid was added dropwise. The mixture was warmed to room temperature, stirred for 2 hours and made basic by addition of 8N caustic soda under ice cooling. The residue was extracted with methylene chloride, dried over sodium sulfate and concentrated. 0.85 g 3-hydrazino-1-methyl-5-trifluoromethylpyrazole was obtained which was treated without further purification.

Workup

  1. stirringstirred for 2 hours
  2. extractionThe residue was extracted with methylene chloride
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0cf1b3986a164750b1000c4c7295c60b
Source dataset
uspto-grants-1995_04
Patent number
US05405829

Reaction notes

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