Dimethylformamide → 4-(6-(1-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)pyridin-2-yl)benzene-1-sulfonyl chloride

HRID 1008834

Reaktionsgleichung

Reaktionsgleichung von HRID 1008834
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[N:21]=[C:20]([C:22]5[CH:27]=[CH:26][C:25]([S:28]([OH:31])(=O)=[O:29])=[CH:24][CH:23]=5)[CH:19]=[CH:18][CH:17]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.O=S(Cl)[Cl:34].CN(C=O)C>O=P(Cl)(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[N:21]=[C:20]([C:22]5[CH:27]=[CH:26][C:25]([S:28]([Cl:34])(=[O:31])=[O:29])=[CH:24][CH:23]=5)[CH:19]=[CH:18][CH:17]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 591663084-(6-(1-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)pyridin-2-yl)benzenesulfonic acid

Produkt 1

HCID 591661084-(6-(1-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)pyridin-2-yl)benzene-1-sulfonyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24813Phosphorus oxychlorideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

4-(6-(1-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)pyridin-2-yl)benzenesulfonic acid (1.9 g, 4.3 mmol) was dissolved in POCl3 (30 mL) followed by the addition of SOCl2 (3 mL) and DMF (100 μl). The reaction mixture was heated at 70-80° C. for 15 min. The volatiles were evaporated and then re-evaporated with chloroform-toluene. The residual brown oil was diluted with chloroform (22 mL) and used for sulfonylation immediately. ESI-MS m/z calc. 456.0, found 457.1 (M+1).

Aufarbeitung

  1. customThe volatiles were evaporated
  2. customre-evaporated with chloroform-toluene
  3. additionThe residual brown oil was diluted with chloroform (22 mL)

Quellen und Nachweise

ORD-Eintrag
ord-901c76fcd3574c7daa1592b3cfffaf30
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973038B2

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