2-Methoxybenzoyl chloride → Methyl 5-[5-(2-methoxyphenyl)[1,2,4]oxadiazol-3-yl]pentanoate

HRID 1039187Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1039187
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](Cl)=[O:6].O[NH:13][C:14]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[NH:15]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]1[O:6][N:15]=[C:14]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])[N:13]=1

Komponenten

4

Edukt 2

HCID 889692-Methoxybenzoyl chlorideHCID 178500328methyl 5-(N-hydroxycarbamimidoyl)pentanoate

Produkt 1

HCID 59167762Methyl 5-[5-(2-methoxyphenyl)[1,2,4]oxadiazol-3-yl]pentanoateAusbeute 34,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Add 2-methoxybenzoyl chloride (5.20 g, 35 mmol) to a solution of methyl 5-(N-hydroxycarbamimidoyl)pentanoate (5.3 g, 34 mmol) in pyridine (50 mL) under nitrogen at 0° C. and then heat the mixture at reflux for 6 h. Remove the solvent under reduced pressure, dilute the residue with ethyl acetate and wash with 1 N HCl. Wash the combined organic extracts with brine, dry over sodium sulfate and remove the solvent under reduced pressure. Purify the residue by flash column chromatography on silica gel, eluting with ethyl acetate/hexanes (1:4), to afford methyl 5-[5-(2-methoxyphenyl)[1,2,4]oxadiazol-3-yl]pentanoate (3.4 g, 33% over two steps): 1H NMR (CDCl3) δ1.7-1.85 (m, 2H), 1.85-2.00 (m, 2H), 2.35 (t, 2H), 2.95 (t, 2H), 3.65 (s, 3H), 3.95 (s, 3H), 7.00 (m, 2H), 7.45 (t, 1H), 8.00 (d, 1H).

Aufarbeitung

  1. temperatureheat the mixture
  2. temperatureat reflux for 6 h
  3. customRemove the solvent under reduced pressure
  4. additiondilute the residue with ethyl acetate
  5. washwash with 1 N HCl
  6. washWash the combined organic extracts with brine
  7. dry with materialdry over sodium sulfate
  8. customremove the solvent under reduced pressure
  9. customPurify the residue by flash column chromatography on silica gel
  10. washeluting with ethyl acetate/hexanes (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-733b23d963614ec089ffcd5e6c985e45
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552039B2

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