m-Chloroperbenzoic acid → 2-Amino-5-(2-pyridylsulfinyl)thiazole

HRID 1656959ノート

反応式

HRID 1656959 の反応式
Cl.Cl.[NH2:3][C:4]1[S:5][C:6]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:7][N:8]=1.ClC1C=CC=C(C(OO)=[O:24])C=1>C(Cl)(Cl)Cl>[NH2:3][C:4]1[S:5][C:6]([S:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[O:24])=[CH:7][N:8]=1

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 189547342-Amino-5-(2-pyridylthio)thiazole dihydrochloride

生成物 1

HCID 101307512-Amino-5-(2-pyridylsulfinyl)thiazole収率 106.5%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

To a solution of 2-amino-5-(2-pyridylthio)thiazole dihydrochloride (4.0 g) in chloroform (100 ml) was dropwise added the solution of 3-chloroperbenzoic acid (5.0 g) in chloroform (100 ml) at 5° C. with stirring. The mixture was stirred at 5° C. for 1.5 hours. The reaction mixture was washed with aqueous sodium bicarbonate and dried over magnesium sulfate. The solvent was concentrated under reduced pressure to give solid. The solid was subjected to column chromatography on silica gel (silica gel 60, 70-230 mesh; Merck: 100 g) and eluted with a mixture of chloroform and methanol (10:1). The fractions containing the objective compound were combined and concentrated under reduced pressure to give 2-amino-5-(2-pyridylsulfinyl)thiazole (3.4 g, yield: 78.9%). mp: 200°-202° C. (dec.) IR (Nujol): 3300, 3150, 1630, 1575, 1270, 1225 cm-1

後処理

  1. stirringThe mixture was stirred at 5° C. for 1.5 hours
  2. washThe reaction mixture was washed with aqueous sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe solvent was concentrated under reduced pressure
  5. customto give solid
  6. washeluted with a mixture of chloroform and methanol (10:1)
  7. additionThe fractions containing the objective compound
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-4b77eb8c7a944b07871a708dcf9317ea
出典データセット
uspto-grants-1993_10
特許番号
US05256675

反応ノート

読み込み中…