Reaktion #569810

Reaktionsgleichung

N-(4-trifluoromethylphenyl)-3-(4-propoxyphenyl)-4-(N-propyl-N-(2,2,2-trichloroethoxycarbonyl)amino)-4,5,-dihydro-1H-pyrazole-1-carboxamide

N-(4-trifluoromethylphenyl)-3-(4-propoxyphenyl)-4-(N-propyl-N-(2,2,2-trichloroethoxycarbonyl)amino)-4,5-dihydro-1H-pyrazole-1-carboxamide

tetrahydrofuran

acetic acid

→

N-(4-trifluoromethylphenyl)-3-(4-propoxyphenyl)-4-(N-propylamino)-4,5,-dihydro-1H-pyrazole-1-carboxamide

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe starting material had been consumed
2. 2
   FiltrationThe mixture was filtered from unreacted zinc
3. 3
   Einengenconcentrated in vacuo
4. 4
   workup.DISSOLUTIONdissolved in 200 ml of diethyl ether
5. 5
   Waschenwashed twice with 100 ml of water
6. 6
   Waschenwashed once with 100 ml of dilute aqueous sodium hydroxide
7. 7
   Waschenwashed once with brine
8. 8
   TrocknenThe resulting ether solution was dried over anhydrous magnesium sulfate
9. 9
   Einengenconcentrated in vacuo
10. 10
    Sonstigechromatographed over silica gel

Vorschrift

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.

Quelle