Potassium Carbonate → phenyl 1-p-Tolyl-3-(trifluoromethyl)-1H-pyrazol-5-ylcarbamate

HRID 631502Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 631502
[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([N:7]2[C:11]([NH2:12])=[CH:10][C:9]([C:13]([F:16])([F:15])[F:14])=[N:8]2)=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:26]>C1COCC1>[C:1]1([CH3:17])[CH:2]=[CH:3][C:4]([N:7]2[C:11]([NH:12][C:25](=[O:26])[O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:10][C:9]([C:13]([F:15])([F:16])[F:14])=[N:8]2)=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 50896499HCID 50896499, Verbindung

Produkt 1

HCID 58267955phenyl 1-p-Tolyl-3-(trifluoromethyl)-1H-pyrazol-5-ylcarbamateAusbeute 104,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

According to the procedure described in Example 161C, to a solution of 1-p-tolyl-3-(trifluoromethyl)-1H-pyrazol-5-amine (2.237 g, 9.57 mmol) in THF (25 mL) and K2CO3 (2.48 g, 18.5 mmol) was added phenyl chloroformate (1.887 g, 12.1 mmol). The crude product was purified by silica gel chromatography with 5-20% EtOAc/hexane as eluants to afford phenyl 1-p-Tolyl-3-(trifluoromethyl)-1H-pyrazol-5-ylcarbamate as solid (3.614 g, 94%). 1H NMR (300 MHz, CDCl3) δ 7.40 (m, 6H), 7.26 (m, 2H), 7.24 (m, 2H), 6.86 (s, 1H), 2.46 (s, 3H); LC-MS (ESI) m/z 362 (M+H)+.

Aufarbeitung

  1. customThe crude product was purified by silica gel chromatography with 5-20% EtOAc/hexane as eluants

Quellen und Nachweise

ORD-Eintrag
ord-5df98247534148efbcdb2c36bbe9b667
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09320739B2

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