3-(4-Chlorophenyl)-4-phenyl-N-[4-(trifluoromethyl)phenyl]-4,5-dihydro-1H-pyrazole-1-carboxamide → HCID 19786515, compound

HRID 1657153Notes

Reaction equation

HRID 1657153 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:14]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[N:13]2)=[O:11])=[CH:5][CH:4]=1.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[F:31][C:2]([F:1])([F:30])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]([C:23]3[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=3)[NH:13]2)=[O:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 30420853-(4-Chlorophenyl)-4-phenyl-N-[4-(trifluoromethyl)phenyl]-4,5-dihydro-1H-pyrazole-1-carboxamideHCID 21225700Diisobutylaluminumhydride3×

Product 1

HCID 19786515HCID 19786515, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To 20.2 g (45 mmole) of N-(4-trifluoromethylphenyl)-3-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamide U.S. Pat. No. 4,156,007, column 7, line 17) in 75 ml of tetrahydrofuran (THF) that had been cooled under a nitrogen atmosphere to -75° C. was added 100 ml of 1.0M diisobutylaluminum hydride (DIBAL-H) in THF. The reaction mixture was warmed to 0° C. and stirred for 1 hour. An additional 50 ml of the 1.0M DIBAL-H solution was added and the reaction was warmed to 20° C. After 1 more hour yet another 50 ml of the 1.0M DIBAL-H solution was added. After stirring at 20° C. for an additional hour the mixture was cooled to 0° C. and carefully quenched with 40 ml of methanol. This mixture was poured onto a mixture of 300 g of ice and 75 ml of 12M aqueous hydrochloric acid. The mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The resulting solid was recrystallized from 600 ml of ethanol to yield 10.4 g of product, mp 212°-214° C.

Workup

  1. temperaturethe reaction was warmed to 20° C
  2. stirringAfter stirring at 20° C. for an additional hour the mixture
  3. temperaturewas cooled to 0° C.
  4. customcarefully quenched with 40 ml of methanol
  5. additionThis mixture was poured onto a mixture of 300 g of ice and 75 ml of 12M aqueous hydrochloric acid
  6. extractionThe mixture was extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe resulting solid was recrystallized from 600 ml of ethanol

Sources & evidence

ORD record
ord-8f8a19808d3747cd9ff9c66c062b7ff9
Source dataset
uspto-grants-1993_10
Patent number
US05256670

Reaction notes

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