Water → 3-Ethyl-5-(5-chloro-6-methylthio-3-pyridyl)-isoxazole

HRID 368292

Reaktionsgleichung

Reaktionsgleichung von HRID 368292
[Cl:1][C:2]1[C:3]([S:10][CH3:11])=[N:4][CH:5]=[C:6]([C:8]#[CH:9])[CH:7]=1.[N+:12]([CH2:15][CH2:16][CH3:17])([O-])=[O:13].C1(N=C=O)C=CC(N=C=O)=CC=1.O>C(N(CC)CC)C.C1C=CC=CC=1>[CH2:16]([C:15]1[CH:9]=[C:8]([C:6]2[CH:5]=[N:4][C:3]([S:10][CH3:11])=[C:2]([Cl:1])[CH:7]=2)[O:13][N:12]=1)[CH3:17]

Komponenten

7

Edukt 4

HCID 962WaterHCID 79031-NitropropaneHCID 610091,4-DiisocyanatobenzeneHCID 232882663-Chloro-5-ethynyl-2-methylthiopyridine

Produkt 1

HCID 232882733-Ethyl-5-(5-chloro-6-methylthio-3-pyridyl)-isoxazoleAusbeute 479,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8471TriethylamineKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture of 3-chloro-5-ethynyl-2-methylthiopyridine (0.5 g, 2.72 mmol), 1-nitropropane (0.24 g, 0.27 mmol), 1,4-phenylenediisocyanate (1.3 g, 7.93 mmol) and triethylamine (5 drops) in benzene (20 mL) was heated under reflux with stirring for 8 hours, and allowed to stir at room temperature overnight. Water (1 mL) was added and the mixture stirred at room temperature for 2 hours. It was filtered through Celite, dried over anhydrous sodium sulphate and evaporated under reduced pressure. Recrystallisation of the residue from hexane gave the desired product (0.33 g, 48%) as a cream solid, melting point. 78-80° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux
  3. stirringto stir at room temperature overnight
  4. stirringthe mixture stirred at room temperature for 2 hours
  5. filtrationIt was filtered through Celite
  6. dry with materialdried over anhydrous sodium sulphate
  7. customevaporated under reduced pressure
  8. customRecrystallisation of the residue from hexane

Quellen und Nachweise

ORD-Eintrag
ord-fde49c4efa35456d916553572faf7e32
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133294

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