Trifluoroacetic anhydride → 5-(N-benzylmethylamino)-4-methyl-2-phenyloxazole

HRID 26492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 26492
[C:1]([NH:9][CH:10]([CH3:22])[C:11]([N:13]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)C)=[O:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:24](F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:16]([CH2:15][NH:13][C:11]1[O:12][C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:9][C:10]=1[CH3:22])[C:21]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:24]=1

Komponenten

5

Edukt 3

HCID 9845Trifluoroacetic anhydrideHCID 10340Sodium CarbonateHCID 213236262-Benzamido-N-benzyl-N-methylpropanamide

Produkt 1

HCID 213236355-(N-benzylmethylamino)-4-methyl-2-phenyloxazoleAusbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

2-Benzamido-N-benzyl-N-methylpropanamide (8.0 g., 0.0269 mol.), was dissolved in dry chloroform (40 ml.) and trifluoroacetic anhydride (17.0 g., 0.0809 mol.) was added dropwise with stirring under nitrogen. The mixture was stirred for 4 hours, then sufficient anhydrous sodium carbonate was added portionwise to neutralise the acid formed. The solid was filtered off and washed with dry chloroform (2× 10 ml.). The combined filtrates were evaporated under reduced pressure to give a brown oil, which was extracted with warm pentane. The pentane solution was evaporated to give a yellow oil 6.20 g. (82.5% IR and NMR confirm the structure.

Aufarbeitung

  1. stirringThe mixture was stirred for 4 hours
  2. customformed
  3. filtrationThe solid was filtered off
  4. washwashed with dry chloroform (2× 10 ml.)
  5. customThe combined filtrates were evaporated under reduced pressure
  6. customto give a brown oil, which
  7. extractionwas extracted with warm pentane
  8. customThe pentane solution was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-2bb484fe08ba41d3b6760dcd31368688
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04150143

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