Dimethylformamide → 1-Phenyl-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl chloride

HRID 475452Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 475452
[C:1]1([N:7]2[C:11]([C:12](O)=[O:13])=[CH:10][C:9]([C:15]([F:18])([F:17])[F:16])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:22])=O.CN(C)C=O>C(Cl)Cl.CN(C)C=O>[C:1]1([N:7]2[C:11]([C:12]([Cl:22])=[O:13])=[CH:10][C:9]([C:15]([F:18])([F:17])[F:16])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 222503231-Phenyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid2×

Produkt 1

HCID 222503331-Phenyl-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A sample of crude 1-phenyl-3-(trifluoromethyl)pyrazole-5-carboxylic acid (i.e. the product of Step B) (4.13 g, 16.1 mmol) was dissolved in methylene chloride (45 mL). The solution was treated with oxalyl chloride (1.80 mL, 20.6 mmol), followed by N,N-dimethylformamide (0.010 mL, 0.13 mmol). Off-gassing began shortly after adding the N,N-dimethylformamide catalyst. The reaction mixture was stirred for ˜20 minutes under ambient conditions, then was heated to reflux for a period of 35 minutes. Volatile were removed by stripping the reaction mixture on a rotary evaporator at a bath temperature of 55° C. The product consisted of 4.43 g of a light-yellow oil. The only impurity observed by 1H NMR was N,N-dimethylformamide.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for a period of 35 minutes
  3. customVolatile were removed
  4. customon a rotary evaporator at a bath temperature of 55° C

Quellen und Nachweise

ORD-Eintrag
ord-c7f1bfc3f0cc43f3bf4a2aa321c85b82
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637552B2

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