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

HRID 516500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 516500
[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. Volatiles 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. customVolatiles were removed
  4. customon a rotary evaporator at a bath temperature of 55° C

Quellen und Nachweise

ORD-Eintrag
ord-8d36ab973e2a4d97ad37baa5fefb71d5
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09113630B2

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