Benzaldehyde → Benzamide, 2-(hydroxyphenylmethyl)-N-methyl-

HRID 46808

Reaktionsgleichung

Reaktionsgleichung von HRID 46808
[CH3:1][NH:2][C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([Li])CCC.[CH:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[OH:23][CH:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:5]1[C:4]([C:3]([NH:2][CH3:1])=[O:10])=[CH:9][CH:8]=[CH:7][CH:6]=1

Komponenten

7

Edukt 4

HCID 240BenzaldehydeHCID 11954N-MethylbenzamideHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Produkt 1

HCID 12241019Benzamide, 2-(hydroxyphenylmethyl)-N-methyl-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a flask equiped with a stirrer, dropping funnel, condenser and gas inlet tube maintained under a nitrogen atmosphere there is added at room temperature 67.5 g. (0.5 mole) N-methyl benzamide and 1200 ml. dry tetrahydrofuran. The reaction flask is immersed in an ice bath and cooled to an internal temperature of 5° C. Stirring is initiated and 688 ml. of 1.6 M. n-butyl lithium (1.1 mole) in hexane is added dropwise over about 1 hour maintaining temperature below 8° C. The resulting dilithio salt is stirred at 5° C. for an additional hour and then a solution of 58.5 g. (0.55 mole) of benzaldehyde in 500 ml. tetrahydrofuran is added dropwise in about 1 hour maintaining the temperature between -10° to +10° C. The resulting mixture is stirred at 5° C. for 1 hour longer and 300 ml. of saturated ammonium chloride is added maintaining the temperature at about 10° C. The layers are separated and the organic phase dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to give α-hydroxy-N-methyl-α-phenyl-o-toluamide.

Aufarbeitung

  1. customTo a flask equiped with a stirrer
  2. temperaturemaintained under a nitrogen atmosphere
  3. additionthere is added at room temperature 67.5 g
  4. customThe reaction flask is immersed in an ice bath
  5. temperaturemaintaining temperature below 8° C
  6. temperaturemaintaining the temperature between -10° to +10° C
  7. stirringThe resulting mixture is stirred at 5° C. for 1 hour longer
  8. temperaturemaintaining the temperature at about 10° C
  9. customThe layers are separated
  10. dry with materialthe organic phase dried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6721723cd52743ab8e7c7fc23665ee85
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04175191

Verknüpfte Notizen

Wird geladen…