Tetrahydrofuran → 4-(4-Chloromethylphenoxymethyl)-5-methyl-2-phenylthiazole

HRID 350011Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350011
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]O)=[CH:21][CH:20]=1.O1CCCC1>C1(C)C=CC=CC=1>[Cl:3][CH2:23][C:22]1[CH:25]=[CH:26][C:19]([O:18][CH2:17][C:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[S:10][C:6]=2[CH3:5])=[CH:20][CH:21]=1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 688862694-(5-Methyl-2-phenyl-4-thiazolylmethoxy)benzyl alcohol

Produkt 1

HCID 178613534-(4-Chloromethylphenoxymethyl)-5-methyl-2-phenylthiazoleAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A solution of thionyl chloride (1.5 mL) in toluene (5 mL) was added to a mixture of 4-(5-methyl-2-phenyl-4-thiazolylmethoxy)benzyl alcohol (4.50 g), tetrahydrofuran (50 mL) and toluene (50 mL) under ice-cooling, which was stirred at room temperature for 2 hours. The reaction mixture was concentrated. The residue was dissolved in ethyl acetate, which was washed with saturated aqueous sodium bicarbonate solution, then with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, and concentrated to obtain colorless crystals of 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenylthiazole (4.50 g, yield 94%). Melting point: 100–101° C.

Aufarbeitung

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwhich was washed with saturated aqueous sodium bicarbonate solution
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-383316e3e8d449daa9ae1ee142d77004
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179823B1

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