Acetic Acid → HCID 18981009, compound

HRID 482610Notes

Reaction equation

HRID 482610 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:16][CH:15]([N:17](C)[C:18](OCC(Cl)(Cl)Cl)=O)[C:14]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)=[N:13]2)=[O:11])=[CH:5][CH:4]=1.O1CCCC1.C(O)(=O)C>CO.[Zn]>[F:35][C:2]([F:1])([F:34])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:16][CH:15]([NH:17][CH3:18])[C:14]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)=[N:13]2)=[O:11])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 18980949HCID 18980949, compound

Product 1

HCID 18981009HCID 18981009, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To 17.3 g (30 mmole) of N-(4-trifluoromethylphenyl)-3-(4-chlorophenyl)-4-(N-methyl-N-(2,2,2-trichloroethoxycarbonyl)amino)-4,5-dihydro-1H-pyrazole-1-carboxamide (Example 115) dissolved in 50 ml of methanol and 50 ml of tetrahydrofuran was added 14 g (233 mmole) of acetic acid and 3.95 g (60 mmole) of zinc dust. After stirring for 1 hour the reaction mixture was filtered, concentrated in vacuo, dissolved in diethyl ether, washed with water, 5% aqueous sodium bicarbonate, and brine and dried over anhydrous magnesium sulfate. Concentration in vacuo and chromatography over silica gel using diethyl ether, hexanes, and ethyl acetate yielded 7.3 g of the compound, of Example 116, a white solid, mp 148°-149° C.

Workup

  1. filtrationwas filtered
  2. concentrationconcentrated in vacuo
  3. dissolutiondissolved in diethyl ether
  4. washwashed with water, 5% aqueous sodium bicarbonate, and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationConcentration in vacuo and chromatography over silica gel

Sources & evidence

ORD record
ord-97825a8c1b1e44428b83826bdb372e9a
Source dataset
uspto-grants-1998_08
Patent number
US05798311

Reaction notes

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