Isamoxole → N-Butyl-N-(5-hydroxy-4-methyl-1,3-oxazol-2-YL)-2-methylpropanamide

HRID 1112392

Reaktionsgleichung

Reaktionsgleichung von HRID 1112392
[CH3:1][C:2]1[N:3]=[C:4]([N:7]([CH2:13][CH2:14][CH2:15][CH3:16])[C:8](=[O:12])[CH:9]([CH3:11])[CH3:10])[O:5][CH:6]=1.ClC1C=CC=C(C(OO)=[O:25])C=1>C(Cl)Cl>[OH:25][C:6]1[O:5][C:4]([N:7]([CH2:13][CH2:14][CH2:15][CH3:16])[C:8](=[O:12])[CH:9]([CH3:11])[CH3:10])=[N:3][C:2]=1[CH3:1]

Komponenten

4

Edukt 2

HCID 42118IsamoxoleHCID 70297m-Chloroperbenzoic acid

Produkt 1

HCID 21323624N-Butyl-N-(5-hydroxy-4-methyl-1,3-oxazol-2-YL)-2-methylpropanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-methyl-2-(N-butyl isobutyramido)oxazole (15 g., 0.067 m.) in dry methylene chloride (100 c.c.) was cooled to 0° C during the addition of m-chloroperbenzoic acid (16 g., 0.023 m.) over 1 hour. The mixture was then stirred at room temperature for 40 hours. The precipitated m-chlorobenzoic acid was then filtered off and the filtrate evaporated to dryness. The residue was taken in ether (100 c.c.) and stirred with 5% aqueous sodium sulphite solution for 1 hour. The organic phase was then separated and washed successively with aqueous sodium carbonate (× 2) and water, and then dried and evaporated to give a brown oil, 13.9 g.

Aufarbeitung

  1. filtrationThe precipitated m-chlorobenzoic acid was then filtered off
  2. customthe filtrate evaporated to dryness
  3. stirringstirred with 5% aqueous sodium sulphite solution for 1 hour
  4. customThe organic phase was then separated
  5. washwashed successively with aqueous sodium carbonate (× 2) and water
  6. customdried
  7. customevaporated
  8. customto give a brown oil, 13.9 g

Quellen und Nachweise

ORD-Eintrag
ord-d7f09e864a7c42dd951ef377e3eddeed
Quelldatensatz
uspto-grants-1978_10
Patentnummer
US04122183

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