3-(Trifluoromethyl)benzoyl chloride → HCID 15220955, compound

HRID 1608960Notes

Reaction equation

HRID 1608960 reaction equation
[C:1]1([CH:7]2[CH:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:10][NH:9][C:8]2=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](Cl)=[O:25]>C(Cl)Cl.N1C=CC=CC=1>[F:19][C:20]([F:30])([F:31])[C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24]([N:10]1[CH:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8](=[O:18])[NH:9]1)=[O:25]

Participants

5

Reactant 2

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 2704924,5-diphenyltetrahydro-3h-pyrazol-3-one

Product 1

HCID 15220955HCID 15220955, compoundYield 24.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4,5-diphenyl-3-pyrazolidinone (2.0 g, 8.4 mmol) in 50 mL CH2Cl2 and 5 mL pyridine was treated dropwise with a solution of 3-trifluoromethylbenzoylchloride (1.4 g, 8.4 mmol) in 25 mL CH2Cl2 and stirred overnight. The mixture was washed with 1N HCl, dried over Na2SO4, evaporated, and the product isolated by chromatography (preparative HPLC) as 840 mg (24%) purple foam:

Workup

  1. washThe mixture was washed with 1N HCl
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-20acf6a6468e45acaac8d670d2b0f7da
Source dataset
uspto-grants-1995_03
Patent number
US05399565

Reaction notes

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