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Sodium hydride → 1-(2-Methyl-1,3,4-thiadiazol-5-ylmethoxy)-4-[2-methyl-2-(2-pyridinyloxy)ethoxy]benzene

HRID 1588301
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1588301
[CH3:1][CH:2]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[H-].[Na+].[CH3:21][C:22]1[S:23][C:24]([CH2:27]Cl)=[N:25][N:26]=1>CN(C=O)C>[CH3:21][C:22]1[S:23][C:24]([CH2:27][O:11][C:8]2[CH:7]=[CH:6][C:5]([O:4][CH2:3][CH:2]([CH3:1])[O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[CH:10][CH:9]=2)=[N:25][N:26]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 15018837Phenol, 4-[2-(2-pyridinyloxy)propoxy]-HCID 155820072-(Chloromethyl)-5-methyl-1,3,4-thiadiazole

Produkt 1

HCID 150188381-(2-Methyl-1,3,4-thiadiazol-5-ylmethoxy)-4-[2-methyl-2-(2-pyridinyloxy)ethoxy]benzeneAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
3×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 4.46 g (18.2 mmol) of 4-[2-methyl-2-(2-pyridinyloxy)ethoxy]phenol in 30 ml of DMF was added to a suspension of 0.6 g (1.1 eq.) of NaH (80% dispersion in mineral oil) in 30 ml of DMF at RT and the mixture was then heated at 80° C. for 1 h. A solution of 2.7 g (18.2 mmol) of 2-methyl-5-chloromethyl-1,3,4-thiadiazole in 20 ml of DMF was added and the mixture was then heated at 120° C. for 6 h. The solvent was stripped off in a rotary evaporator, the residue was taken up in ethyl acetate, and the solution was washed three times with water. Drying, removal of the solvent and purification of the crude product by chromatography (silica gel, cyclohexane/ethyl acetate 2:1) resulted in 2.9 g (45%) of colorless crystals; melting point 72°-78° C.

Aufarbeitung

  1. temperaturethe mixture was then heated at 120° C. for 6 h
  2. customThe solvent was stripped off in a rotary evaporator
  3. washthe solution was washed three times with water
  4. customDrying
  5. customremoval of the solvent and purification of the crude product by chromatography (silica gel, cyclohexane/ethyl acetate 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-1533e62508c842118e907ce869bb0079
Quelldatensatz
uspto-grants-1993_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05221684

Notizen zur Reaktion

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