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Phenobarbital → 5-Ethyl-6-hydroxy-3-(4-methoxycarbonylbutyl)-5-phenyl-2,4(3H,5H)-pyrimidinedione

HRID 1450141
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1450141
[CH3:1][CH2:2][C:3]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:10](=[O:11])[NH:9][C:7](=[O:8])[NH:6][C:4]1=[O:5].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.Br[CH2:37][CH2:38][CH2:39][CH2:40][C:41]([O:43][CH3:44])=[O:42].[Cl-].[Na+]>ClCCl>[CH2:2]([C:3]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]([OH:11])=[N:9][C:7](=[O:8])[N:6]([CH2:37][CH2:38][CH2:39][CH2:40][C:41]([O:43][CH3:44])=[O:42])[C:4]1=[O:5])[CH3:1]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 4763PhenobarbitalHCID 5234Sodium ChlorideHCID 79557Methyl 5-bromovalerateHCID 2723671Tetrabutylammonium Hydroxide

Produkt 1

HCID 1784352455-Ethyl-6-hydroxy-3-(4-methoxycarbonylbutyl)-5-phenyl-2,4(3H,5H)-pyrimidinedione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

A mixture of phenobarbital (46.5 g, 0.2 mole) and tetrabutylammonium hydroxide (500 mL, 0.2 mole of 0.4M in water) in dichloromethane (500 mL) was prepared and to it was added methyl 5-bromovalerate (39.0 g, 0.2 mole). The reaction mixture was stirred vigorously overnight (20 hrs). To this mixture was added saturated sodium chloride solution (100 mL), the organic layer was separated, and the aqueous solution was washed with dichloromethane (2×100 mL). The combined organic solution was washed with saturated sodium chloride solution (100 mL), dried over anhydrous MgSO4, filtered, and the solvent removed.

Aufarbeitung

  1. customwas prepared and to it
  2. customthe organic layer was separated
  3. washthe aqueous solution was washed with dichloromethane (2×100 mL)
  4. washThe combined organic solution was washed with saturated sodium chloride solution (100 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customthe solvent removed

Quellen und Nachweise

ORD-Eintrag
ord-8952355646a94cbca3eb341036e71988
Quelldatensatz
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05601994

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