Chlorosuccinimide → 5-Chloro-2-formylamino-4-(4-formylaminophenylthiomethyl)thiazole

HRID 2380614ノート

反応式

HRID 2380614 の反応式
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([CH2:9][S:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][CH:18]=[O:19])=[CH:13][CH:12]=2)[N:8]=1)=[O:2].[Cl:20]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:20][C:6]1[S:5][C:4]([NH:3][CH:1]=[O:2])=[N:8][C:7]=1[CH2:9][S:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][CH:18]=[O:19])=[CH:13][CH:12]=1

参加物

4

反応物 2

HCID 31398ChlorosuccinimideHCID 157291722-Formylamino-4-(4-formylaminophenylthiomethyl)thiazole

生成物 1

HCID 157291735-Chloro-2-formylamino-4-(4-formylaminophenylthiomethyl)thiazole収率 61.2%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
50 °C

実験手順

To a solution of 2-formylamino-4-(4-formylaminophenylthiomethyl)thiazole (2.9 g) in acetic acid (30 ml) was portionwise added N-chlorosuccinimide at 50° C. with stirring. The mixture was heated at 50° C. with stirring. The reaction mixture was concentrated under reduced pressure and the residue was triturated with water. The mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran (1:1), washed with water 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: 150 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 5-chloro-2-formylamino 4(4-formylaminophenylthiomethyl)thiazole (2.0 g yield: 61.2%).

後処理

  1. customat 50° C.
  2. stirringwith stirring
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was triturated with water
  5. extractionThe mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran (1:1)
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe solvent was concentrated under reduced pressure
  9. customto give solid
  10. washeluted with a mixture of chloroform and methanol (10:1)
  11. additionThe fractions containing the objective compound
  12. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-9be42dcf392840bc942ba164074d4546
出典データセット
uspto-grants-1994_11
特許番号
US05369107

反応ノート

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