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

HRID 1192782Notes

Reaction equation

HRID 1192782 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-9939b6b3e41949748bea1a9b23d7f922
Source dataset
uspto-grants-2014_03
Patent number
US08680269B2

Reaction notes

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