Triethylamine → 4-(5-Oxazolyl)-benzamide

HRID 1186895Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1186895
[O:1]1[C:5]([C:6]2[CH:14]=[CH:13][C:9]([C:10](O)=[O:11])=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1.CC[N:17](CC)CC.ClC(OCC(C)C)=O.[NH4+].[OH-]>C1COCC1>[O:1]1[C:5]([C:6]2[CH:14]=[CH:13][C:9]([C:10]([NH2:17])=[O:11])=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 62365Isobutyl chloroformateHCID 27764144-(1,3-Oxazol-5-yl)benzoic Acid

Produkt 1

HCID 219309994-(5-Oxazolyl)-benzamideAusbeute 48,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 4-(5-oxazolyl)benzoic acid (1.0 g, 5.46 mmol) and Et3N (552 mg, 5.46 mmol) in 25 mL of THF was cooled to 0° C. and ClCOOi-Bu (745 mg, 5.46 mmol) was added dropwise. After the addition was over, the reaction mixture was stirred for additional 5 min and then aq NH4OH (0.63 mL of 28% solution, 10.46 mmol) was added. After overnight stirring, the solvent was evaporated, the residue was taken up in water and basified to pH 9. The precipitated solid was filtered, washed with water and dried over P2O5 in a vacuum desiccator to provide 500 mg (48%) of the 4-(5-oxazolyl)-benzamide: 1H NMR (DMSO-d6) δ 8.50 (s, 1H), 8.20-7.80 (m, 5H).

Aufarbeitung

  1. additionAfter the addition
  2. stirringAfter overnight stirring
  3. customthe solvent was evaporated
  4. filtrationThe precipitated solid was filtered
  5. washwashed with water
  6. dry with materialdried over P2O5 in a vacuum desiccator

Quellen und Nachweise

ORD-Eintrag
ord-55340db12f9f41ad833e99f65f62e6d7
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673924B2

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