3-Chloropropionyl chloride → 1-(4-Trifluoromethoxyphenyl)-pyrazolidin-3-one

HRID 708938Notes

Reaction equation

HRID 708938 reaction equation
Cl.[F:2][C:3]([F:14])([F:13])[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][NH2:12])=[CH:7][CH:6]=1.Cl[CH2:16][CH2:17][C:18](Cl)=[O:19].CCN(C(C)C)C(C)C>C1COCC1>[F:2][C:3]([F:13])([F:14])[O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:17][C:18](=[O:19])[NH:12]2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 693643-Chloropropionyl chlorideHCID 81531DiisopropylethylamineHCID 27773284-(Trifluoromethoxy)phenylhydrazine hydrochloride

Product 1

HCID 669570351-(4-Trifluoromethoxyphenyl)-pyrazolidin-3-oneYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound was prepared according to Rees and Tsoi Chem. Commun. 2000, 415. A suspension of (4-trifluoromethoxyphenyl)-hydrazine hydrochloride (300 mg, 1.32 mmol, 1.00 eq), 3-chloropropionyl chloride (167 mg, 1.32 mmol, 1.00 eq), and PS-DIEA (1.30 grams (g), 5.28 mmol, 4.00 eq) in THF (20 mL) was stirred at ambient temperature for 12 h. The solution was then filtered, concentrated to dryness, and purified via chromatography (2:2:1, hexane:EtOAc:acetone) to afford the desired intermediate (120 mg, 37%).

Workup

  1. customThe compound was prepared
  2. filtrationThe solution was then filtered
  3. concentrationconcentrated to dryness
  4. custompurified via chromatography (2:2:1, hexane:EtOAc:acetone)

Sources & evidence

ORD record
ord-b93f590554fd447e87127c2100338bc4
Source dataset
uspto-grants-2015_11
Patent number
US09179681B2

Reaction notes

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