Methanol → 2-Acetylamino-4-(naphth-1-yl)oxazole

HRID 33563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 33563
[NH2:1][C:2]1[O:3][CH:4]=[C:5]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][CH:8]=2)[N:6]=1.C(N(CC)CC)C.[C:24](Cl)(=[O:26])[CH3:25].CO>ClCCl>[C:24]([NH:1][C:2]1[O:3][CH:4]=[C:5]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][CH:8]=2)[N:6]=1)(=[O:26])[CH3:25]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 6367Acetyl chloride2×HCID 8471TriethylamineHCID 103079572-Amino-4-(naphth-1-yl)oxazole

Produkt 1

HCID 597968402-Acetylamino-4-(naphth-1-yl)oxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a cooled (ice/salt bath) mixture of 2-amino-4-(naphth-1-yl)oxazole (1)(0.5 g) and triethylamine (0.8 ml) in anhydrous dichloromethane (5 ml) was added dropwise acetyl chloride (0.2 ml) over a minute. The resulting mixture was warmed to room temperature and left overnight. Further acetyl chloride (0.1 ml) was added and the mixture left for a further hour. Dichloromethane (40 ml) and few drops of methanol were added. The mixture was washed twice with brine, dried with sodium sulphate, filtered and evaporated in vacuo. The title compound (9) (0.35 g; m.p. 188-190° C.) was obtained following silica gel column chromatography of the residue in 2% methanol in chloroform.

Aufarbeitung

  1. temperatureTo a cooled
  2. waitthe mixture left for a further hour
  3. washThe mixture was washed twice with brine
  4. dry with materialdried with sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4a542a07cdbf48b783167e4decab0fd8
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429607B2

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