Acetic Acid → HCID 18980984, compound

HRID 482613Notes

Reaction equation

HRID 482613 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:16][CH:15]([NH:17]C(OCC(Cl)(Cl)Cl)=O)[C:14]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)=[N:13]2)=[O:11])=[CH:5][CH:4]=1.C(O)(=O)C>CO.O1CCCC1.[Zn]>[F:34][C:2]([F:1])([F:33])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:16][CH:15]([NH2:17])[C:14]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)=[N:13]2)=[O:11])=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 18980978HCID 18980978, compound

Product 1

HCID 18980984HCID 18980984, compoundYield 43.5%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 20 g (36 mmole) of N-(4-trifluoromethylphenyl)-3-(4-chlorophenyl)-4-(N-(2,2,2-trichloroethoxycarbonyl)amino)-4,5-dihydro-1H-pyrazole-1-carboxamide (Example 154) in 50 ml of methanol and 50 ml of tetrahydrofuran was added 4.69 g (72 mmole) of zinc dust and 16 g (267 mmole) of acetic acid. After stirring for 1 hour the reaction was filtered, concentrated in vacuo, partitioned between diethyl ether and water, washed with 5% aqueous sodium bicarbonate, washed with brine, dried over anhydrous magnesium sulfate, concentrated in vacuo, and chromatographed on silica gel using methylene chloride and ethyl acetate to yield 6 g of the title compound, a white solid, mp 144°-146° C.

Workup

  1. filtrationwas filtered
  2. concentrationconcentrated in vacuo
  3. custompartitioned between diethyl ether and water
  4. washwashed with 5% aqueous sodium bicarbonate
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customchromatographed on silica gel

Sources & evidence

ORD record
ord-ea1e6f6f701d4735a3c040bc87586ad3
Source dataset
uspto-grants-1998_08
Patent number
US05798311

Reaction notes

Loading…