Benzoyl isothiocyanate → HCID 86631470, Verbindung

HRID 335089Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 335089
[NH2:1][C:2]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=2[Cl:20])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][C:5]([Br:21])=[CH:4][N:3]=1.[C:22]([N:30]=[C:31]=[S:32])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[C:22]([NH:30][C:31](=[S:32])[NH:1][C:2]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=2[Cl:20])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][C:5]([Br:21])=[CH:4][N:3]=1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

4

Edukt 2

HCID 68284Benzoyl isothiocyanateHCID 66994785Ethyl 3-(2-amino-5-bromopyridin-3-yloxy)-4-chlorobenzoate

Produkt 1

HCID 86631470HCID 86631470, VerbindungAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Ethyl 3-(2-amino-5-bromopyridin-3-yloxy)-4-chlorobenzoate (9.645 g, 25.95 mmol) and benzoyl isothiocyanate (4.659 g, 28.55 mmol) were placed in THF (250 mL) and the reaction mixture was stirred at room temperature for 18 hours, then heated at 55° C. for two days. THF was removed and the residue was purified by silica gel chromatography (5-25% EtOAc in hexane) to provide ethyl 3-(2-(3-benzoylthioureido)-5-bromopyridin-3-yloxy)-4-chlorobenzoate (7.08 g, 51.0%) as a yellow solid.

Aufarbeitung

  1. temperatureheated at 55° C. for two days
  2. customTHF was removed
  3. customthe residue was purified by silica gel chromatography (5-25% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ab2b4f3a638d49ff88c5e76a47c4ff8f
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883828B2

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