Methanol → N-(2,5-Dimethylphenyl)acetamide

HRID 475932

Reaktionsgleichung

Reaktionsgleichung von HRID 475932
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH2:4].[C:10](OC(=O)C)(=[O:12])[CH3:11].CO>O1CCCC1>[CH3:9][C:6]1[CH:7]=[CH:8][C:2]([CH3:1])=[C:3]([NH:4][C:10]([CH3:11])=[O:12])[CH:5]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 72592,5-DimethylanilineHCID 7918Acetic Anhydride

Produkt 1

HCID 16304N-(2,5-Dimethylphenyl)acetamideAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2,5-Dimethylaniline 16 (5.0 gm, 0.041 moles) was dissolved in 30 ml tetrahydrofuran (THF) at room temperature under argon. Acetic anhydride (5.9 ml, 0.062 moles) was added. Within 15 minutes, solids formed and the mixture became a solid white mass after 1 hour. Methanol was added which dissolved the mass. The mixture was evaporated under reduced pressure, dissolved in hot DCM and purified by flash chromatography on silica gel, eluting with a mixture of methanol and DCM. 2,5-Dimethylacetanilide 17 (6.67 gm, 99% yield) was isolated after removing the solvent. NMR (CDCl3) δ 7.53, 1H, br s; 6.89-7.06, 3H, m; 2.30, 3H, s; 2.19, 3H, s; 2.17, 3H, s.

Aufarbeitung

  1. customsolids formed
  2. customafter 1 hour
  3. dissolutiondissolved the mass
  4. customThe mixture was evaporated under reduced pressure
  5. dissolutiondissolved in hot DCM
  6. custompurified by flash chromatography on silica gel
  7. washeluting with a mixture of methanol and DCM

Quellen und Nachweise

ORD-Eintrag
ord-7029fc6668fe4910a3e1e246048c1d9f
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637658B2

Verknüpfte Notizen

Wird geladen…