5-Fluoro-2-(trifluoromethyl)benzoyl chloride → (2Z)-2-(3-butyl-4-methyl-1,3-thiazol-2(3H)-ylidene)-1-[5-fluoro-2-(trifluoromethyl)phenyl]ethanone

HRID 448033Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 448033
[I-].[CH2:2]([N+:6]1[C:10]([CH3:11])=[CH:9][S:8][C:7]=1[CH3:12])[CH2:3][CH2:4][CH3:5].[F:13][C:14]1[CH:15]=[CH:16][C:17]([C:23]([F:26])([F:25])[F:24])=[C:18]([CH:22]=1)[C:19](Cl)=[O:20]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CS(C)=O.CO>[CH2:2]([N:6]1[C:10]([CH3:11])=[CH:9][S:8]/[C:7]/1=[CH:12]\[C:19]([C:18]1[CH:22]=[C:14]([F:13])[CH:15]=[CH:16][C:17]=1[C:23]([F:26])([F:24])[F:25])=[O:20])[CH2:3][CH2:4][CH3:5]

Komponenten

6

Edukt 2

HCID 27375605-Fluoro-2-(trifluoromethyl)benzoyl chlorideHCID 691651093-Butyl-2,4-dimethylthiazol-3-ium iodide

Produkt 1

HCID 69323879(2Z)-2-(3-butyl-4-methyl-1,3-thiazol-2(3H)-ylidene)-1-[5-fluoro-2-(trifluoromethyl)phenyl]ethanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel3×HCID 22036561Dimethyl sulfoxide methanolLösungsmittel

Versuchsvorschrift

In a 20 mL vial a solution of 3-butyl-2,4-dimethylthiazol-3-ium iodide (47.92 mg, 0.16 mmol) dissolved in CH2Cl2 (0.5 mL) was added, followed by the addition of DMAP (49.24 mg, 0.40 mmol) dissolved in CH2Cl2 (0.8 mL). Then, to the solution was added 5-fluoro-2-(trifluoromethyl)benzoyl chloride (36.2 mg, 0.16 mmol) dissolved in CH2Cl2 (0.5 mL). The vial was capped and shaken overnight at room temperature. The residue was dissolved 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, MS and LC/MS. 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 0.90 (t, 3 H) 1.29-1.38 (m, 2H) 1.56-1.69 (m, 2 H) 2.28-2.32 (m, 3 H) 3.91-4.00 (m, 2 H) 6.00-6.05 (m, 1 H) 6.58-6.62 (m, 1 H) 7.37-7.45 (m, 2 H) 7.77-7.86 (m, 1 H); MS (ESI) positive ion 360 (M+H).

Aufarbeitung

  1. additionwas added
  2. customThe vial was capped
  3. custompurified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-cf158add023d49bcbc3b85582b60203f
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481574B2

Notizen zur Reaktion

Wird geladen…