Benzoyl isothiocyanate → Ethyl 3-(2-(3-benzoylthioureido)-5-bromopyridin-4-yloxy)-4-chlorobenzoate

HRID 911036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 911036
[NH2:1][C:2]1[CH:7]=[C:6]([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])[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[CH:7]=[C:6]([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])[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 66617810Ethyl 3-(2-amino-5-bromopyridin-4-yloxy)-4-chlorobenzoate

Produkt 1

HCID 86634758Ethyl 3-(2-(3-benzoylthioureido)-5-bromopyridin-4-yloxy)-4-chlorobenzoateAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A flask was charged with ethyl 3-(2-amino-5-bromopyridin-4-yloxy)-4-chlorobenzoate (2.76 g, 7.43 mmol), benzoyl isothiocyanate (1.05 ml, 7.80 mmol) and THF (100 mL). The reaction mixture was stirred at ambient temperature overnight and then concentrated. The residue was purified by silica gel column chromatography using 20% ether in hexanes to give the desired product (1.35 g, 34% yield) as light yellow solid.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-65a12d81dda8438aa19fc2c304257d6e
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022222B2

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