Thionyl Chloride → 4-Tert-butyl-2-[5-(2-chloromethylphenylthiomethyl)benzofuran-2-yl]thiazole

HRID 487694Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 487694
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][S:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH2:27]O)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:31])=O.C(=O)([O-])O.[Na+]>CN(C)C=O.C(Cl)(Cl)Cl>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][S:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH2:27][Cl:31])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 190927354-Tert-butyl-2-[5-(2-hydroxymethylphenylthiomethyl)benzofuran-2-yl]thiazole

Produkt 1

HCID 190927004-Tert-butyl-2-[5-(2-chloromethylphenylthiomethyl)benzofuran-2-yl]thiazoleAusbeute 136,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of 4-tert-butyl-2-[5-(2-hydroxymethylphenylthiomethyl)benzofuran-2-yl]thiazole (0.42 g), thionyl chloride (0.1 g) and N,N-dimethylformamide (3 drops) in chloroform (5 ml) was stirred for 3 hours at ambient temperature. The resulting mixture was poured into aqueous sodium hydrogen carbonate solution and extracted with chloroform. The extract was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give 4-tert-butyl-2-[5-(2-chloromethylphenylthiomethyl)benzofuran-2-yl]thiazole (0.49 g).

Aufarbeitung

  1. extractionextracted with chloroform
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bd6ecbab1e954832bd33f6cba098e4a1
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05296495

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