Acetyl chloride → N-acetyl-N-methyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide

HRID 1789356ノート

反応式

HRID 1789356 の反応式
[H-].[Na+].[CH3:3][NH:4][C:5]([N:7]1[CH2:11][CH2:10][S:9][CH:8]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=2)[CH2:23][CH2:22]1)=[O:6].[C:34](Cl)(=[O:36])[CH3:35]>CN(C)C=O.CCOCC>[C:34]([N:4]([CH3:3])[C:5]([N:7]1[CH2:11][CH2:10][S:9][CH:8]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH2:19][CH2:20][N:21]1[CH2:22][CH2:23][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=2)[CH2:25][CH2:26]1)=[O:6])(=[O:36])[CH3:35]

参加物

6

反応物 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 13767930HCID 13767930、化合物

生成物 1

HCID 13768041N-acetyl-N-methyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

0.1 g of sodium hydride (60% oil dispersion) is added to a solution of one g of N-methyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide in 30 ml of dimethylformamide, and a solution of 0.19 g of acetyl chloride in 5 ml of ether is added thereto. After the mixture is stirred at 50° C. for 20 hours, the mixture is concentrated under reduced pressure to remove solvent. Water is added to the residue, and the aqueous mixture is extracted with ethyl acetate. The extract is washed with water, dried and then concentrated under reduced pressure to remove solvent. The residue is purified by silica gel chromatography (solvent, ethyl acetate:n-hexane=4:1). 0.32 g of N-acetyl-N-methyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide is obtained as an oil.

後処理

  1. concentrationthe mixture is concentrated under reduced pressure
  2. customto remove solvent
  3. additionWater is added to the residue
  4. extractionthe aqueous mixture is extracted with ethyl acetate
  5. washThe extract is washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customto remove solvent
  9. customThe residue is purified by silica gel chromatography (solvent, ethyl acetate:n-hexane=4:1)

出典と根拠

ORDレコード
ord-cc5689b69bf7423889aa61414394c6d6
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…