2,6-Difluorobenzoyl chloride → (2Z)-2-(3-butyl-4,5-dimethyl-1,3-thiazol-2(3H)-ylidene)-1-(2,6-difluorophenyl)ethanone

HRID 448070Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 448070
[I-].[CH2:2]([N+:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:7]=1[CH3:13])[CH2:3][CH2:4][CH3:5].[F:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:16]=1[C:17](Cl)=[O:18]>CN(C1C=CN=CC=1)C>[CH2:2]([N:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8]/[C:7]/1=[CH:13]\[C:17]([C:16]1[C:15]([F:14])=[CH:23][CH:22]=[CH:21][C:20]=1[F:24])=[O:18])[CH2:3][CH2:4][CH3:5]

Komponenten

4

Edukt 2

HCID 874382,6-Difluorobenzoyl chlorideHCID 691655913-Butyl-2,4,5-trimethylthiazol-3-ium iodide

Produkt 1

HCID 69322289(2Z)-2-(3-butyl-4,5-dimethyl-1,3-thiazol-2(3H)-ylidene)-1-(2,6-difluorophenyl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 142844-(Dimethylamino)pyridineKatalysator

Versuchsvorschrift

In a 20 mL vial 3-butyl-2,4,5-trimethylthiazol-3-ium iodide (48 mg in 0.5 mL DMA, 0.16 mmol, 1 equiv.) was added, followed by TEA (38 mg in 0.5 mL DMA, 0.37 mmol, 2.4 equiv.) and the solution went black. DMAP (2 mg in 0.5 mL DMA, 0.016 mmol, 0.1 equiv) was added next, followed by 2,6-difluorobenzoyl chloride (0.9 mL of 0.2M in DMA, 1.2 equiv). The mixture was shaken overnight at room temperature and then concentrated in vacuo. The resulting residue was taken up in 1:1 DMSO/MeOH and purified by reverse phase HPLC using a method analogous to that described in Example 53 to provide the title compound. 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 0.89 (t, 3 H) 1.28-1.38 (m, 2 H) 1.55-1.64 (m, 2 H) 2.20 (s, 3 H) 2.22 (s, 3 H) 3.91-3.96 (m, 2 H) 6.03 (s, 1 H) 7.07-7.15 (m, 2 H) 7.39-7.47 (m, 1 H); MS (ESI) m/z 324 (M+H)+.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. custompurified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-dc0ac779c9a84d1fab7757a4999feda7
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481574B2

Notizen zur Reaktion

Wird geladen…