Cyclohexanecarbonyl chloride → (2Z)-2-(3-butyl-4-methyl-1,3-thiazol-2(3H)-ylidene)-1-cyclohexylethanone

HRID 448030Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 448030
[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].[CH:13]1([C:19](Cl)=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>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]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:20])[CH2:3][CH2:4][CH3:5]

Komponenten

6

Edukt 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 691651093-Butyl-2,4-dimethylthiazol-3-ium iodide

Produkt 1

HCID 24955354(2Z)-2-(3-butyl-4-methyl-1,3-thiazol-2(3H)-ylidene)-1-cyclohexylethanone

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 cyclohexanecarbonyl chloride (23.5 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) 1.09-1.44 (m, 7 H) 1.51-1.70 (m, 3 H) 1.69-1.88 (m, 4 H) 2.21-2.36 (m, 4 H) 3.95-4.01 (m, 2 H) 5.79-5.91 (m, 1 H) 6.57-6.73 (m, 1 H) MS (ESI) positive ion 280 (M+H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-6723b46411c84ee8a8b22065c6f55ab3
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481574B2

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