5-Fluoro-2-methylbenzoyl chloride → (2Z)-2-(3-butyl-4-methyl-1,3-thiazol-2(3H)-ylidene)-1-(5-fluoro-2-methylphenyl)ethanone

HRID 448034Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 448034
[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]([CH3:23])=[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]([F:13])[CH:15]=[CH:16][C:17]=1[CH3:23])=[O:20])[CH2:3][CH2:4][CH3:5]

Komponenten

6

Edukt 2

HCID 27373835-Fluoro-2-methylbenzoyl chlorideHCID 691651093-Butyl-2,4-dimethylthiazol-3-ium iodide

Produkt 1

HCID 69324003(2Z)-2-(3-butyl-4-methyl-1,3-thiazol-2(3H)-ylidene)-1-(5-fluoro-2-methylphenyl)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-methylbenzoyl chloride (27.6 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 0.92 (t, 3 H) 1.28-1.41 (m, 2 H) 1.57-1.68 (m, 2 H) 2.28-2.31 (m, 3 H) 2.33-2.36 (m, 3 H) 3.92-4.03 (m, 2 H) 6.09-6.15 (m, 1 H) 6.54-6.59 (m, 1 H) 7.05-7.14 (m, 1 H) 7.19-7.27 (m, 2 H);); MS (ESI) positive ion 306 (M+H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-304b61c8b0b4423cb165bb5842ccb13e
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481574B2

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