Dimethyl Sulfoxide → HCID 59334473, Verbindung

HRID 1639741Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1639741
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]1[N:22]=[C:15]2[C:16]([CH2:20][OH:21])=[CH:17][CH:18]=[CH:19][N:14]2[N:13]=1.C(N(CC)CC)C>ClCCl>[CH3:11][C:12]1[N:22]=[C:15]2[C:16]([CH:20]=[O:21])=[CH:17][CH:18]=[CH:19][N:14]2[N:13]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 59334623HCID 59334623, Verbindung

Produkt 1

HCID 59334473HCID 59334473, VerbindungAusbeute 83.613,297 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Under nitrogen atmosphere, to a solution of oxalyl chloride (16.0 mL, 180 mmol) in dichloromethane (200 mL) was added dimethyl sulfoxide (30.0 mL, 0.420 mol) at −78° C., and the mixture was stirred for 30 min. To the reaction mixture was added a solution of (2-methyl[1,2,4]triazolo[1,5-a]pyridin-8-yl)methanol (23.0 g, 0.141 mmol) in dichloromethane (82 mL), and the mixture was stirred for 2 hr. To the reaction mixture was added triethylamine (99.0 mL, 0.710 mol) at −78° C., and the mixture was stirred for 1 hr and warmed to room temperature. After concentration under reduced pressure, the residue was purified by silica gel column chromatography (methanol/ethyl acetate=1/10) to give the title compound (19.0 g, yield 84%).

Aufarbeitung

  1. stirringthe mixture was stirred for 2 hr
  2. stirringthe mixture was stirred for 1 hr
  3. concentrationAfter concentration under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate=1/10)

Quellen und Nachweise

ORD-Eintrag
ord-206ee832da734f589bc198df39e57e5d
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110585B2

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