Dimethylamine → HCID 4467695, Verbindung

HRID 1446154Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1446154
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]([C:13](O)=[O:14])=[C:11]([CH3:16])[O:10][N:9]=1.S(Cl)(Cl)=O.[CH3:21][NH:22][CH3:23]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]([C:13]([N:22]([CH3:23])[CH3:21])=[O:14])=[C:11]([CH3:16])[O:10][N:9]=1

Komponenten

4

Edukt 3

HCID 674DimethylamineHCID 24386Thionyl ChlorideHCID 902034-Isoxazolecarboxylic acid, 3-(2-chlorophenyl)-5-methyl-

Produkt 1

HCID 4467695HCID 4467695, VerbindungAusbeute 23,6 %

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To 3-(2-chlorophenyl)-5-methylisoxazol-4-carboxylic acid (25 mg, 0.10 mmol) was added thionyl chloride (1 mL) and the neat solution allowed to stir 60° C. After 30 min, excess thionyl chloride was evaporated and dimethyl amine (40 μL, 0.08 mmol, 2M in tetrahydrofuran) was added and allowed to stir overnight at ambient temperature. The residue was purified using reversed phase HPLC to afford the title compound (5 mg). HRMS (ESI, pos. ion) m/z calcd for C13H13ClN2O2: 264.0666, found 264.0669.

Aufarbeitung

  1. customexcess thionyl chloride was evaporated
  2. stirringto stir overnight at ambient temperature
  3. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-0d5037ad7476428a856729169b98b565
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666888B2

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