Sodium Iodide → N-methyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide

HRID 1789347ノート

反応式

HRID 1789347 の反応式
[CH3:1][NH:2][C:3]([N:5]1[CH2:9][CH2:8][S:7][CH:6]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16])=[O:4].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:30][CH2:29]1>CN(C)C=O>[CH3:1][NH:2][C:3]([N:5]1[CH2:9][CH2:8][S:7][CH:6]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:30][CH2:29]1)=[O:4]

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 47418781-(2-Chloroethyl)-4-phenylpiperazineHCID 137496082-(2-Hydroxyphenyl)-N-methyl-1,3-thiazolidine-3-carboxamide

生成物 1

HCID 13767927N-methyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide収率 44.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of 2.38 g of N-methyl-2-(2-hydroxyphenyl)thiazolidine-3-carboxamide, 1.38 g of potassium carbonate, 0.7 g of sodium iodide, 3.36 g of 1-(2-chloroethyl)-4-phenylpiperazine and 25 ml of dimethylformamide is stirred at 90° C. for 24 hours. The mixture is concentrated under reduced pressure to remove dimethylformamide. Water is added to the residue, and the aqueous mixture is extacted with ethyl acetate. The extract is washed with dilute sodium hydroxide solution and water, successively. The ethyl acetate solution is dried and then concentrated under reduced pressure to remove solvent. The residue is purified by silica gel chromatography (sovent, benzene:ethyl acetate-1:5). 1.89 g of N-methyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide are obtained.

後処理

  1. concentrationThe mixture is concentrated under reduced pressure
  2. customto remove dimethylformamide
  3. additionWater is added to the residue
  4. washThe extract is washed with dilute sodium hydroxide solution and water
  5. dry with materialThe ethyl acetate solution is dried
  6. concentrationconcentrated under reduced pressure
  7. customto remove solvent
  8. customThe residue is purified by silica gel chromatography (sovent, benzene:ethyl acetate-1:5)

出典と根拠

ORDレコード
ord-99a2331c88664704a50a163db33a54cd
出典データセット
uspto-grants-1987_08
特許番号
US04689327

反応ノート

読み込み中…