Thionyl Chloride → 5-Chloromethyl-2-(2-phenyl-4-thiazolylmethoxy)pyridine

HRID 349977

反応式

HRID 349977 の反応式
[C:1]1([C:7]2[S:8][CH:9]=[C:10]([CH2:12][O:13][C:14]3[N:19]=[CH:18][C:17]([CH2:20]O)=[CH:16][CH:15]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:24])=O>>[Cl:24][CH2:20][C:17]1[CH:16]=[CH:15][C:14]([O:13][CH2:12][C:10]2[N:11]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[S:8][CH:9]=2)=[N:19][CH:18]=1

参加物

3

反応物 2

HCID 24386Thionyl ChlorideHCID 229307412-(2-Phenyl-4-thiazolylmethoxy)-5-pyridylmethanol

生成物 1

HCID 229307835-Chloromethyl-2-(2-phenyl-4-thiazolylmethoxy)pyridine収率 76%

実験手順

A mixture of 6-(2-phenyl-4-thiazolylmethoxy)-3-pyridylmethanol (2.98 g) and thionyl chloride (15 ml) was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium bicarbonate solution was added to the residue, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography to obtain 5-chloromethyl-2-(2-phenyl-4-thiazolylmethoxy)pyridine (2.40 g, yield 76%) as colorless crystals from the fraction eluted with ethyl acetate. This was recrystallized from tetrahydrofuran-hexane. Melting point: 117–118° C.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium bicarbonate solution
  2. additionwas added to the residue, which
  3. extractionwas extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-246dea5476394e2fb4a32963b4c8066e
出典データセット
uspto-grants-2007_02
特許番号
US07179823B1

関連ノート

読み込み中…