Water → 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid N',N'-dimethyl-hydrazide

HRID 471373Notes

Reaction equation

HRID 471373 reaction equation
[CH3:1][N:2]([CH3:4])[NH2:3].[Cl:5][C:6]1[CH:7]=[C:8]([C:13]2([C:28]([F:31])([F:30])[F:29])[O:17][N:16]=[C:15]([C:18]3[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[C:20]([CH3:27])[CH:19]=3)[CH2:14]2)[CH:9]=[C:10]([Cl:12])[CH:11]=1.O.[OH-].[Na+]>CCOCC>[CH3:1][N:2]([CH3:4])[NH:3][C:22](=[O:23])[C:21]1[CH:25]=[CH:26][C:18]([C:15]2[CH2:14][C:13]([C:8]3[CH:9]=[C:10]([Cl:12])[CH:11]=[C:6]([Cl:5])[CH:7]=3)([C:28]([F:31])([F:30])[F:29])[O:17][N:16]=2)=[CH:19][C:20]=1[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 59761,1-DimethylhydrazineHCID 14798Sodium HydroxideHCID 866114794-(5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methylbenzoyl chloride

Product 1

HCID 674425084-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid N',N'-dimethyl-hydrazideYield 71.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of N,N-dimethyl hydrazine (0.55 g) in ether (46 mL) was added 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoyl chloride (2.00 g) in small portions at 0° C. After 50 min at this temperature, water was added and the pH was adjusted to 7 by addition of NaOH (2 M). The organic layer was separated and the aqueous layer was extracted with ether. Combined organic layers were washed with NaHCO3 solution, dried over Na2SO4 and evaporated to give the title compound (1.50 g, 71%).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ether
  3. washCombined organic layers were washed with NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-f826dd07b8314314ac9ea0ae293a0fd8
Source dataset
uspto-grants-2014_01
Patent number
US08633134B2

Reaction notes

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