Salicylamide → HCID 11682447、化合物

HRID 427282ノート

反応式

HRID 427282 の反応式
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C(O[CH:14](OCC)[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH:24]2[S:28][C:27](=[O:29])[NH:26][C:25]2=[O:30])=[CH:19][CH:18]=1)C>C(Cl)(Cl)Cl>[O:9]=[C:1]1[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[O:4][CH:14]([CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])=[CH:21][CH:22]=2)[NH:10]1

参加物

4

反応物 2

HCID 5147SalicylamideHCID 232983485-[4-(2,2-Diethoxyethoxy)benzyl]thiazolidine-2,4-dione

生成物 1

HCID 11682447HCID 11682447、化合物収率 82%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

To a stirred solution of polyphosphonate ethyl ester (PPE) (3.15 g, 7.29 mmol) in chloroform (4.0 mL) was added salicylamide (0.5 g, 3.65 mmol) followed by addition of a solution of 5-[4-[(2,2-diethoxy)ethoxy]phenyl methyl]thiazolidin-2,4-dione (1.36 g, 4.0 mmol) obtained in example 2, in chloroform (10 mL) dropwise at 25-30° C. The reaction mixture was immersed in a preheated oil bath and refluxed for 3 h. The reaction mixture was cooled to room temperature and CHCl3 was removed under reduced pressure. To the resultant residue aq. sat. NaHCO3 solution (25 mL) was added and stirred for 30 min. at 25-30° C. The precipitated brown coloured solid was filtered and purified by column chromatography using EtOAc:pet. ether (1:1) to yield the title compound (1.15 g, 81%). mp: 134° C.-138° C.

後処理

  1. customThe reaction mixture was immersed in a preheated oil bath
  2. temperaturerefluxed for 3 h
  3. customCHCl3 was removed under reduced pressure
  4. additionTo the resultant residue aq. sat. NaHCO3 solution (25 mL) was added
  5. filtrationThe precipitated brown coloured solid was filtered
  6. custompurified by column chromatography

出典と根拠

ORDレコード
ord-359284a9cdfb4d7bb1d6c40f12b2d0d0
出典データセット
uspto-grants-2001_11
特許番号
US06313113B1

反応ノート

読み込み中…