Methylhydrazine → Ethyl 3-difluoromethyl-1-methyl-4-pyrazole carboxylate

HRID 547967Notes

Reaction equation

HRID 547967 reaction equation
F[B-](F)(F)F.[F:6][CH:7]([F:22])[C:8](=[N+:19](C)C)/[C:9](/[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10]\[N:11](C)[CH3:12].CNN>C(#N)C>[F:6][CH:7]([F:22])[C:8]1[C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][N:11]([CH3:12])[N:19]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 178472002[(E)-3-(dimethylamino)-2-ethoxycarbonyl-4,4-difluorobut-2-enylidene]-dimethylazanium tetrafluoroborate

Product 1

HCID 11644126Ethyl 3-difluoromethyl-1-methyl-4-pyrazole carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

10.0 g (30 mmol) of N-[(2E)-1-(difluoromethyl)-3-(dimethylamino)-2-(ethoxycarbonyl)prop-2-en-1-ylidene]-N-methylmethanaminium tetrafluoroborate were dissolved in 50 ml of acetonitrile and admixed with 2.3 g of methylhydrazine. After stirring at RT for 2 h, the acetonitrile was removed completely under reduced pressure. Distillation under reduced pressure or crystallization from n-hexane afforded 5.3 g (86% of theory) of the product having an m.p. of 63-65° C.

Workup

  1. customthe acetonitrile was removed completely under reduced pressure
  2. distillationDistillation
  3. customunder reduced pressure or crystallization from n-hexane
  4. customafforded 5.3 g (86% of theory) of the product

Sources & evidence

ORD record
ord-7fdf5d01d81a4c53b28ce68e38b82729
Source dataset
uspto-grants-2011_05
Patent number
US07939673B2

Reaction notes

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