3-Nitrobenzaldehyde → 2-Hydroxyethyl 3,4,5,8-tetrahydro-6-methyl-8-(3-nitrophenyl)-1,1-dioxo-2H-thiopyrano [3,2-b]pyridine-7-carboxylate

HRID 231348Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 231348
[S:1]1(=[O:9])(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=O)[CH2:2]1.[N+:10]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O)([O-:12])=[O:11].[OH:21][CH2:22][CH2:23][O:24][C:25](=[O:30])/[CH:26]=[C:27](\[NH2:29])/[CH3:28].C([O-])(=O)C.[NH4+]>C(O)C>[CH3:28][C:27]1[NH:29][C:3]2[CH2:4][CH2:5][CH2:6][S:1](=[O:9])(=[O:8])[C:2]=2[CH:16]([C:15]2[CH:18]=[CH:19][CH:20]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=2)[C:26]=1[C:25]([O:24][CH2:23][CH2:22][OH:21])=[O:30]

Komponenten

6

Edukt 4

HCID 74493-NitrobenzaldehydeHCID 517165Ammonium AcetateHCID 11815935Dihydro-2H-thiopyran-3(4H)-one-1,1-dioxideHCID 19980851HCID 19980851, Verbindung

Produkt 1

HCID 140112132-Hydroxyethyl 3,4,5,8-tetrahydro-6-methyl-8-(3-nitrophenyl)-1,1-dioxo-2H-thiopyrano [3,2-b]pyridine-7-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of tetrahydrothiopyran-3-one-1,1-dioxide (2.80 g, 0.0189 moles), 3-nitrobenzaldehyde (2.85 g, 0.0189 moles), 2-hydroxyethyl-3-aminocrotonate (3.28 g, 0.0226 moles), ammonium acetate (0.291 g, 0.0038 moles) and ethanol (35 mL) was refluxed for 16 hours. After cooling to room temperature the resulting solid was isolated by filtration, washed with ethanol and diethyl ether. The product was dried under vacuum for 16 hours at room temperature affording the product; mp 233°-235° C.

Aufarbeitung

  1. temperaturewas refluxed for 16 hours
  2. customwas isolated by filtration
  3. washwashed with ethanol and diethyl ether
  4. customThe product was dried under vacuum for 16 hours at room temperature
  5. customaffording the product

Quellen und Nachweise

ORD-Eintrag
ord-fca93793333646b4ac4f9ad83b353c20
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04845225

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