5-Chloro-2-fluorobenzoyl chloride → (2Z)-2-(3-butyl-4-methyl-1,3-thiazol-2(3H)-ylidene)-1-(5-chloro-2-fluorophenyl)ethanone

HRID 448035

Reaktionsgleichung

Reaktionsgleichung von HRID 448035
[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].[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([F:23])=[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]([Cl:13])[CH:15]=[CH:16][C:17]=1[F:23])=[O:20])[CH2:3][CH2:4][CH3:5]

Komponenten

6

Edukt 2

HCID 27736045-Chloro-2-fluorobenzoyl chlorideHCID 691651093-Butyl-2,4-dimethylthiazol-3-ium iodide

Produkt 1

HCID 69321127(2Z)-2-(3-butyl-4-methyl-1,3-thiazol-2(3H)-ylidene)-1-(5-chloro-2-fluorophenyl)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-chloro-2-fluorobenzoyl chloride (30.9 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 (500 MHz, DMSO-d6/D2O) δ ppm 0.95 (t, 3 H) 1.31-1.41 (m, 2 H) 1.57-1.77 (m, 2 H) 2.28-2.34 (m, 3 H) 3.95-4.02 (m, 2 H) 6.37-6.41 (m, 1 H) 6.55-6.68 (m, 1 H) 7.28-7.35 (m, 1 H) 7.48-7.54 (m, 1 H) 7.76-7.80 (m, 1 H); MS (ESI) positive ion 326 (M+H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-44b24e79dbd443248ff86fd9a24d2e62
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481574B2

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