Acetic Acid → HCID 18980999, compound

HRID 482628Notes

Reaction equation

HRID 482628 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:16][CH:15]([N:17]([CH2:26][CH2:27][CH3:28])C(OCC(Cl)(Cl)Cl)=O)[C:14]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][CH3:38])=[CH:31][CH:30]=3)=[N:13]2)=[O:11])=[CH:5][CH:4]=1.O1CCCC1.C(O)(=O)C>[Zn].CO>[F:40][C:2]([F:1])([F:39])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:16][CH:15]([NH:17][CH2:26][CH2:27][CH3:28])[C:14]([C:29]3[CH:30]=[CH:31][C:32]([O:35][CH2:36][CH2:37][CH3:38])=[CH:33][CH:34]=3)=[N:13]2)=[O:11])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 18980966HCID 18980966, compound

Product 1

HCID 18980999HCID 18980999, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To 22 g (35 mmole) of N-(4-trifluoromethylphenyl)-3-(4-propoxyphenyl)-4-(N-propyl-N-(2,2,2-trichloroethoxycarbonyl)amino)-4,5,-dihydro-1H-pyrazole-1-carboxamide (Example 585) was added 100 ml of tetrahydrofuran, 100 ml of methanol, 4.6 g (70 mmole) of zinc dust, and finally 6.4 g (106 mmole) of acetic acid. After stirring for 2 hours, the starting material had been consumed as shown by TLC. The mixture was filtered from unreacted zinc, concentrated in vacuo, dissolved in 200 ml of diethyl ether, washed twice with 100 ml of water, washed once with 100 ml of dilute aqueous sodium hydroxide and washed once with brine. The resulting ether solution was dried over anhydrous magnesium sulfate, concentrated in vacuo, and chromatographed over silica gel using hexanes, diethyl ether, and ethyl acetate yielding 1 g of N-(4-trifluoromethylphenyl)-3-(4-propoxyphenyl)-4-(N-propyl-N-(2,2-dichloroethoxycarbonyl)-amino)-4,5,-dihydro-1H-pyrazole-1-carboxamide and 12 g of the desired compound, mp 130°-133° C.

Workup

  1. customthe starting material had been consumed
  2. filtrationThe mixture was filtered from unreacted zinc
  3. concentrationconcentrated in vacuo
  4. dissolutiondissolved in 200 ml of diethyl ether
  5. washwashed twice with 100 ml of water
  6. washwashed once with 100 ml of dilute aqueous sodium hydroxide
  7. washwashed once with brine
  8. dry with materialThe resulting ether solution was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customchromatographed over silica gel

Sources & evidence

ORD record
ord-8f0ab468ea834f7098ba761e111a5592
Source dataset
uspto-grants-1998_08
Patent number
US05798311

Reaction notes

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