Trifluoroacetic anhydride → 1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carbonitrile

HRID 2174290Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2174290
[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[N:8][C:7]([C:15]([NH2:17])=O)=[N:6]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[N:8][C:7]([C:15]#[N:17])=[N:6]1

Komponenten

5

Edukt 3

HCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 690939441-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carboxamide

Produkt 1

HCID 690942931-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carbonitrileAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of 1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carboxamide (Intermediate-4, 0.86 mmol) in pyridine (3.0 mL) at 0° C. was treated with trifluoroacetic anhydride (2 equiv) dropwise over the course of 5 min. The reaction was then warmed to ambient temperature and stirred for 2 h. The reaction mixture was poured into saturated NaHCO3 solution and extracted with CH2Cl2. The organic phases were dried over MgSO4, filtered and conc. The crude product was purified using SiO2 chromatography and an appropriate solvent gradient (EtOAc/hexanes) to give 1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazole-3-carbonitrile as white solid (88% yield).

Aufarbeitung

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic phases were dried over MgSO4
  3. filtrationfiltered
  4. customconc. The crude product was purified

Quellen und Nachweise

ORD-Eintrag
ord-46375e3f141d4441ac624cdb2dea3297
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09061030B2

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