Thionyl Chloride → 5-Chloromethyl-2-(2-thienyl)benzoxazole

HRID 322296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 322296
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([CH2:15]O)=[CH:11][C:9]=2[N:10]=1.S(Cl)([Cl:19])=O>>[Cl:19][CH2:15][C:12]1[CH:13]=[CH:14][C:8]2[O:7][C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[N:10][C:9]=2[CH:11]=1

Komponenten

3

Edukt 2

HCID 24386Thionyl ChlorideHCID 156622712-(2-Thienyl)-5-benzoxazolylmethanol

Produkt 1

HCID 220097205-Chloromethyl-2-(2-thienyl)benzoxazoleAusbeute 85 %

Versuchsvorschrift

To 2-(2-thienyl)-5-benzoxazolylmethanol (600 mg) was added thionyl chloride (3 ml) at 0° C., stirred for 3 hours. The reaction mixture was concentrated, which was neutalized with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure to give crystals of 5-chloromethyl-2-(2-thienyl) benzoxazole (550 mg, 85%). The recrystalization from ethyl acetate-hexane gave colorless needles, mp 152-153° C.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4d05bbe3297d41e392666d465a4561c8
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211215B1

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