m-Chloroperbenzoic acid → 2-Amino-4-methyl-5-(2-pyridylsulfinyl)thiazole

HRID 1656990ノート

反応式

HRID 1656990 の反応式
[NH2:1][C:2]1[S:3][C:4]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[C:5]([CH3:7])[N:6]=1.ClC1C=CC=C(C(OO)=[O:23])C=1>C(Cl)(Cl)Cl.ClCCl>[NH2:1][C:2]1[S:3][C:4]([S:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:23])=[C:5]([CH3:7])[N:6]=1

参加物

5

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 189547352-Amino-4-methyl-5-(2-pyridylthio)thiazole

生成物 1

HCID 157291892-Amino-4-methyl-5-(2-pyridylsulfinyl)thiazole収率 52.2%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
5 °C

実験手順

A mixture of 2-amino-4-methyl-5-(2-pyridylthio)thiazole (1.7 g) and 3-chloroperbenzoic acid (1.8 g) in a mixture of chloroform (20 ml) and dichloromethane (50 ml) was stirred at 5° C. for 3.5 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-4-methyl-5-(2-pyridylsulfinyl)thiazole (0.95 g, yield: 52.2 %). mp: 190°-193° C. (dec.)

後処理

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

出典と根拠

ORDレコード
ord-3d40e69cefd048dc94fa9772c97cb315
出典データセット
uspto-grants-1993_10
特許番号
US05256675

反応ノート

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