Water → 5-Trifluoromethyl-4-chloro-3-(3'-dimethylhydrazino-4'-nitrophenoxy)-1-methylpyrazole

HRID 1089043Notes

Reaction equation

HRID 1089043 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:11][N:12]([CH3:14])[CH3:13])[CH:3]=1.[F:15][C:16]([F:26])([F:25])[C:17]1[N:21]([CH3:22])[N:20]=[C:19]([OH:23])[C:18]=1[Cl:24].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[F:26][C:16]([F:15])([F:25])[C:17]1[N:21]([CH3:22])[N:20]=[C:19]([O:23][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:11][N:12]([CH3:14])[CH3:13])[CH:3]=2)[C:18]=1[Cl:24]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 150173004-Fluoro-2-(2,2-dimethylhydrazino) nitrobenzeneHCID 178481948HCID 178481948, compound

Product 1

HCID 150172925-Trifluoromethyl-4-chloro-3-(3'-dimethylhydrazino-4'-nitrophenoxy)-1-methylpyrazoleYield 97.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

1.98 g (0.01 mol) of the product of step (a) was mixed with 2.2 g (0.011 mol) of 5-trifluoromethyl-4- chloro-3-hydroxy-1-methylpyrazole and 1.65 g of potassium carbonate in 15 ml of DMSO and heated for 24 hours at 90° C. The mixture was poured into 400 ml of H2O and extracted with ether. The organic layer was separated, washed with H2O, brine, dried over MgSO4 and solvent removed to give 3.7 g of solid, m.p. 72°-76° C.

Workup

  1. extractionextracted with ether
  2. customThe organic layer was separated
  3. washwashed with H2O, brine
  4. dry with materialdried over MgSO4 and solvent
  5. customremoved

Sources & evidence

ORD record
ord-6e7acb2d51a14cae9c26ec836402a35f
Source dataset
uspto-grants-1990_10
Patent number
US04964895

Reaction notes

Loading…