Triethylamine → N-(3-Cyano-4-neopentyloxyphenyl)-1(3-trifluoromethylphenyl)-5-methylpyrazole-4-carboxamide

HRID 1744559Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1744559
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([N:9]2[C:13]([CH3:14])=[C:12]([C:15]([OH:17])=O)[CH:11]=[N:10]2)[CH:6]=[CH:7][CH:8]=1.[NH2:20][C:21]1[CH:22]=[CH:23][C:24]([O:29][CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[C:25]([CH:28]=1)[C:26]#[N:27].C(N(CC)CC)C.P(C#N)(OCC)(OCC)=O>O.CN(C)C=O>[C:26]([C:25]1[CH:28]=[C:21]([NH:20][C:15]([C:12]2[CH:11]=[N:10][N:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:19])[F:18])[CH:4]=3)[C:13]=2[CH3:14])=[O:17])[CH:22]=[CH:23][C:24]=1[O:29][CH2:30][C:31]([CH3:33])([CH3:32])[CH3:34])#[N:27]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 106357135-methyl-1-[3-(trifluoromethyl)phenyl]-1H-pyrazole-4-carboxylic acidHCID 178227345-Amino-2-neopentyloxybenzonitrile

Produkt 1

HCID 9955685N-(3-Cyano-4-neopentyloxyphenyl)-1(3-trifluoromethylphenyl)-5-methylpyrazole-4-carboxamideAusbeute 41,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-(3-Trifluoromethylphenyl)-5-methylpyrazole-4-carboxylic acid (2 g), 5-amino-2-neopentyloxybenzonitrile (1.8 g), triethylamine (1.6 g) and diethyl cyanophosphate (1.4 g) were added to dimethylformamide (20 ml) and the mixture was stirred at room temperature for 1 h. The reaction mixture was added into water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. n-Hexane was added to the residue to allow crystallization. The crystals were recrystallized from hydrous ethanol to give the title compound (1.4 g), melting point: 116–118° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customafter which the solvent was evaporated under reduced pressure
  5. additionn-Hexane was added to the residue
  6. customcrystallization
  7. customThe crystals were recrystallized from hydrous ethanol

Quellen und Nachweise

ORD-Eintrag
ord-44be4f1c7e804986908c8e36801ae917
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07015218B1

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