Trifluoroacetic acid → HCID 18980914, compound

HRID 482599Notes

Reaction equation

HRID 482599 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][C:15]([NH:18]C(OC(C)(C)C)=O)([CH3:17])[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.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[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][C:15]([NH2:18])([CH3:17])[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

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18980916HCID 18980916, compound

Product 1

HCID 18980914HCID 18980914, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 74 g (149 mmole) of N-(4-trifluoromethylphenyl)-3-(4-chlorophenyl)-4-carbo-t-butoxyamino-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide (Example 2) was added 74 g of trifluoroacetic acid and 74 g of chloroform. The mixture was refluxed for 40 minutes while gas was evolved and then an additional 20 minutes. The mixture was then concentrated in vacuo and then partitioned between ethyl ether and dilute aqueous sodium hydroxide. The organic layer was washed with brine, dried over magnesium sulfate, concentrated in vacuo, and the resulting solid was triturated with hexanes and filtered yielding 50 g (85%) of a white solid, mp 165°-167° C.

Workup

  1. temperatureThe mixture was refluxed for 40 minutes while gas
  2. customan additional 20 minutes
  3. concentrationThe mixture was then concentrated in vacuo
  4. custompartitioned between ethyl ether and dilute aqueous sodium hydroxide
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customthe resulting solid was triturated with hexanes
  9. filtrationfiltered

Sources & evidence

ORD record
ord-abba4acf22284afa91f728a33e547ceb
Source dataset
uspto-grants-1998_08
Patent number
US05798311

Reaction notes

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