Cyanoacetamide → Isopropyl 4-(5-cyano-4-(methylthio)-6-oxo-1,6-dihydropyridin-2-yl)benzoate

HRID 81076Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 81076
[CH3:1][CH:2]([CH3:4])[O-:3].[Na+].CS[C:8]([S:22][CH3:23])=[CH:9][C:10]([C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=O)=[CH:14][CH:13]=1)=O.[C:24]([CH2:26][C:27]([NH2:29])=[O:28])#[N:25]>C(O)(C)C>[C:24]([C:26]1[C:27](=[O:28])[NH:29][C:10]([C:12]2[CH:13]=[CH:14][C:15]([C:16]([O:3][CH:2]([CH3:4])[CH3:1])=[O:18])=[CH:20][CH:21]=2)=[CH:9][C:8]=1[S:22][CH3:23])#[N:25]

Komponenten

5

Edukt 3

HCID 7898CyanoacetamideHCID 109204432-Propanol, sodium salt (1:1)HCID 86665698Methyl 4-(3,3-bis(methylthio)acryloyl)benzoate

Produkt 1

HCID 66927077Isopropyl 4-(5-cyano-4-(methylthio)-6-oxo-1,6-dihydropyridin-2-yl)benzoateAusbeute 79,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel2×

Versuchsvorschrift

A 12% isopropanol suspension of sodium isopropoxide (9.08 g, 13.28 mmol) was added to a mixture of methyl 4-(3,3-bis(methylthio)acryloyl)benzoate (2.5 g, 8.85 mmol) and 2-cyanoacetamide (0.744 g, 8.85 mmol) in isopropanol (50 mL). The resultant mixture was heated to 100° C. for 3 h, cooled to room temperature and quenched with 0.3 N HCl (50 mL). The brown precipitate was collected by filtration, washed with water (10 mL) and dried under vacuum to give isopropyl 4-(5-cyano-4-(methylthio)-6-oxo-1,6-dihydropyridin-2-yl)benzoate (2.3 g, 63% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.70-8.42 (4H, m), 6.67 (1H, br. s), 4.89-5.43 (1H, m), 1.10-1.64 (6H, m); MS (ES+) m/z: 329 (M+H); LC retention time: 3.18 min (analytical HPLC Method A).

Aufarbeitung

  1. customquenched with 0.3 N HCl (50 mL)
  2. filtrationThe brown precipitate was collected by filtration
  3. washwashed with water (10 mL)
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ed71303c0ccf4073873f724e31f2551b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846673B2

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