Dimethylformamide → Phenobarbital

HRID 1658881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1658881
[CH3:1][CH2:2][C:3]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9](=[O:10])[N:8]=[C:7]([O-:11])[NH:6][C:4]1=[O:5].[Na+].ClCC([O-])=O.[Na+].[Cl-].[Cl-].[Ca+2].CN(C=O)C>CO>[CH3:1][CH2:2][C:3]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:9](=[O:10])[NH:8][C:7](=[O:11])[NH:6][C:4]1=[O:5]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 5284359Calcium ChlorideHCID 23665759Sodium chloroacetateHCID 23674889Phenobarbital sodium

Produkt 1

HCID 4763PhenobarbitalAusbeute 36,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of sodium phenobarbitone (8.8 g, 35 mmoles), and sodium chloroacetate (4.5 g, 38 mmoles) in methanol (250 ml) was mixed with a solution of CaCl2 (3 g) in methanol (50 ml). After addition of 5 ml DMF the mixture was refluxed for 36 hours. After removal of the solvent, the residue was treated with water (100 ml) and acidified with conc. HCl followed by extraction with chloroform. The organic layer was evaporated to dryness and the residue treated with 10% NaHCO3 solution. Extraction with chloroform and evaporation of the organic layer yielded 3 g of unreacted phenobarbital. The bicarbonate layer was acidified with conc. HCl and extracted with chloroform. Evaporation of the dried (MgSO4) chloroform yielded 4.5 g of a gummy material which solidified slowly on standing. TLC and NMR showed this to be nearly pure monoacid with only traces of unreacted phenobarbitone and dialkylated derivative.

Aufarbeitung

  1. temperaturewas refluxed for 36 hours
  2. customAfter removal of the solvent
  3. additionthe residue was treated with water (100 ml)
  4. extractionfollowed by extraction with chloroform
  5. customThe organic layer was evaporated to dryness
  6. additionthe residue treated with 10% NaHCO3 solution
  7. extractionExtraction
  8. customwith chloroform and evaporation of the organic layer

Quellen und Nachweise

ORD-Eintrag
ord-3aa01259f1e54672891c1ba34032acac
Quelldatensatz
uspto-grants-1976_06
Patentnummer
US03966744

Notizen zur Reaktion

Wird geladen…