Salicylamide → 2-(2-Methylpropoxy)benzamide

HRID 1288264

Reaktionsgleichung

Reaktionsgleichung von HRID 1288264
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[Na].[CH2:12](Br)[CH:13]([CH3:15])[CH3:14]>C(O)C>[CH2:12]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([NH2:10])=[O:9])[CH:13]([CH3:15])[CH3:14]

Komponenten

5

Edukt 3

HCID 5147SalicylamideHCID 65551-Bromo-2-methylpropaneHCID 5360545Sodium

Produkt 1

HCID 49464332-(2-Methylpropoxy)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Salicylamide (68.5 g.; prepared as described by R. Bogoczek, Farm. Polska, 1960, 16, 26) was added to a solution of sodium (11.5 g.) in anhydrous ethanol (400 ml.). Isobutyl bromide (60 ml.) was then added, and the mixture was stirred and heated to reflux overnight. The ethanol was evaporated, and sufficient water was added to the residue to dissolve the sodium bromide. The oil which did not dissolve was extracted with chloroform, the extract was washed twice with 2N sodium hydroxide solution and once with water, dried over magnesium sulphate, filtered and evaporated. The residue was triturated with light petroleum (b.p. 40°-60° C.) to give 2-isobutoxybenzamide, which was pure enough for use in the next stage of the synthesis. A pure sample, m.p. 125°-128° C., was obtained by recrystallisation of an aliquot from cyclohexane.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customThe ethanol was evaporated
  4. additionsufficient water was added to the residue
  5. dissolutionto dissolve the sodium bromide
  6. dissolutionThe oil which did not dissolve
  7. extractionwas extracted with chloroform
  8. washthe extract was washed twice with 2N sodium hydroxide solution and once with water
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was triturated with light petroleum (b.p. 40°-60° C.)

Quellen und Nachweise

ORD-Eintrag
ord-e85522e5c58742ffa7d9f7068f609f70
Quelldatensatz
uspto-grants-1976_10
Patentnummer
US03987160

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