p-Toluenesulfonic acid → HCID 178515487, Verbindung

HRID 923340Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 923340
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([NH2:13])[NH:10][N:9]=2)=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1.[O:25]1[C:29]2[CH:30]=[CH:31][C:32]([C:34](=O)[CH2:35][C:36](OCC)=[O:37])=[CH:33][C:28]=2[O:27][CH2:26]1>C1(OC2C=CC=CC=2)C=CC=CC=1>[O:25]1[C:29]2[CH:30]=[CH:31][C:32]([C:34]3[NH:13][C:11]4[N:10]([N:9]=[C:8]([C:5]5[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=5)[N:12]=4)[C:36](=[O:37])[CH:35]=3)=[CH:33][C:28]=2[O:27][CH2:26]1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 2756586Ethyl 3-(2H-1,3-benzodioxol-5-yl)-3-oxopropanoateHCID 178508293HCID 178508293, Verbindung

Produkt 1

HCID 178515487HCID 178515487, VerbindungAusbeute 24,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7583Diphenyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

To a solution of 3-(4-chlorophenyl)-1H-1,2,4-triazol-5-amine (50 mg, 0.26 mmol) in diphenyether (2 ml) was added TsOH (2.2 mg, 0.01 mmol) and ethyl 3-(benzo[d][1,3]dioxol-5-yl)-3-oxopropanoate (81 mg, 0.34 mmol). After stirring 2 h at 170° C., the reaction was quenched by the addition of hexane (5 ml), the product was collected by filtration and washed with methanol (10 ml) and dried in an oven under reduced pressure to give 5-(benzo[d][1,3]dioxol-5-yl)-2-(4-chlorophenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7(4H)-one as a off-white solid (23.1 mg, 24%).

Aufarbeitung

  1. customthe reaction was quenched by the addition of hexane (5 ml)
  2. filtrationthe product was collected by filtration
  3. washwashed with methanol (10 ml)
  4. customdried in an oven under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-30ae433dc90c4542a6920ffa4431b565
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278973B2

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