Water → HCID 178434613, compound

HRID 82310Notes

Reaction equation

HRID 82310 reaction equation
C[NH:2][C:3]([CH3:21])=[C:4]([C:15](=O)[C:16]([F:19])([F:18])[F:17])[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].O.[NH2:23]N.O.C([O-])(O)=O.[Na+]>C1COCC1.C(O)(=O)C.CCOC(C)=O>[CH3:21][C:3]1[C:4]([C:5]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:6])=[C:15]([C:16]([F:19])([F:18])[F:17])[NH:23][N:2]=1

Participants

8

Reactant 4

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 178483593HCID 178483593, compound

Product 1

HCID 178434613HCID 178434613, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl 3-(methylamino)-2-(trifluoroacetyl)but-2-enoate (90 g, 300 mmol) in a mixture of THF (900 mL) and acetic acid (100 mL) was added hydrazine monohydrate (14.6 mL, 300 mmol) over a 5 min period. The reaction mixture was heated to reflux for 3 hours, allowed to cool to room temperature and the solvents were evaporated in vacuo to afford a bright yellow mass. The mass was dissolved in EtOAc (1 L) and water (1 L) with gentle heating, allowed to cool to room temperature and the aqueous layer was neutralized to pH 7-8 with NaHCO3. This mixture was transferred to a 3-L separating funnel, the layers were mixed vigorously, separated and the organic layer was washed with water (3×500 mL) dried (MgSO4), filtered and evaporated in vacuo to give benzyl 3-methyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate as an off-white solid in 89% yield 74 g that was used without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. customthe solvents were evaporated in vacuo
  4. customto afford a bright yellow mass
  5. temperatureto cool to room temperature
  6. customseparating funnel
  7. additionthe layers were mixed vigorously
  8. customseparated
  9. washthe organic layer was washed with water (3×500 mL)
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-b545c12b023d4278a04a10a304bc18ee
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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