Diethyl Ether → HCID 86760337, Verbindung

HRID 859143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 859143
CCO/C(/C)=[N:5]\[O:6][S:7]([C:10]1[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=1[CH3:18])(=[O:9])=[O:8].[Cl:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:22]=1[C:29]1[C:34]([CH3:35])=[CH:33][CH:32]=[CH:31][N:30]=1.C(OCC)C>O1CCOCC1.C(Cl)Cl>[CH3:16][C:15]1[CH:14]=[C:13]([CH3:17])[CH:12]=[C:11]([CH3:18])[C:10]=1[S:7]([O-:9])(=[O:8])=[O:6].[NH2:5][N+:30]1[CH:31]=[CH:32][CH:33]=[C:34]([CH3:35])[C:29]=1[C:22]1[CH:23]=[CH:24][C:25]([O:27][CH3:28])=[CH:26][C:21]=1[Cl:20]

Komponenten

6

Edukt 3

HCID 3283Diethyl EtherHCID 5748625ethyl (1E)-N-{[(2,4,6-trimethylphenyl)sulfonyl]oxy}ethanimidateHCID 42624977HCID 42624977, Verbindung

Produkt 1

HCID 86760337HCID 86760337, VerbindungAusbeute 138,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A 0° C. solution of ethyl O-mesitylsulfonylacetohydroxamate (4.68 g, 16.4 mmol) in dioxane (10 mL) was treated with HClO4 (1.8 mL, 20.8 mmol) dropwise over 25 minutes. The reaction was stirred at 0° C. for two hours then poured into ice H2O and stirred vigorously for 30 minutes. The mixture was filtered and the filter cake dissolved in CH2Cl2. The CH2Cl2 solution was washed with cold H2O and passed through a plug of anhydrous K2CO3 directly into a flask containing a 0° C. solution of 2-(2-chloro-4-methoxyphenyl)-3-methylpyridine (1.37 g, 5.9 mmol) in CH2Cl2 (15 mL). The reaction was allowed to stir overnight at room temperature. Diethyl ether was added to the reaction and it was concentrated in vacuo to give a white foam (3.66 g) which was used as is in the next step: MS m/z 249.16 (M++H).

Aufarbeitung

  1. stirringstirred vigorously for 30 minutes
  2. filtrationThe mixture was filtered
  3. dissolutionthe filter cake dissolved in CH2Cl2
  4. washThe CH2Cl2 solution was washed with cold H2O
  5. custompassed through a plug of anhydrous K2CO3 directly into a flask
  6. stirringto stir overnight at room temperature
  7. concentrationwas concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-79174e8dceed48109ecdfd370606a313
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07151109B2

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