Dimethyl Sulfoxide → 2-[3-(4-Phenylpiperazin-1-yl)propylthio]benzaldehyde

HRID 1789372ノート

反応式

HRID 1789372 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]1([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][S:26][C:27]3[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=3[CH2:29][OH:30])[CH2:19][CH2:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl.O>[C:11]1([N:17]2[CH2:18][CH2:19][N:20]([CH2:23][CH2:24][CH2:25][S:26][C:27]3[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=3[CH:29]=[O:30])[CH2:21][CH2:22]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 137680822-[3-(4-Phenylpiperazin-1-yl)propylthio]benzylalcohol

生成物 1

HCID 201881712-[3-(4-Phenylpiperazin-1-yl)propylthio]benzaldehyde収率 90.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

A solution of 1.1 g of dimethylsulfoxide in 5 ml of methylene chloride is added to a solution of 0.894 g of oxalyl chloride in 20 ml of methylene chloride at -50° C. A solution of 2.19 g of 2-[3-(4-phenylpiperazin-1-yl)propylthio]benzylalcohol in 10 ml of methylene chloride is added to the mixture at -50° C., and the mixture is stirred at the same temperature for 15 minutes. 3.24 g of triethylamine are added to the mixture, and the mixture is stirred at -50° C. for 5 minutes and further stirred at room temperature for one hour. The mixture is poured into water, and the aqueous mixture is extracted with methylene chloride. The extract is washed with water, dried and concentrated under reduced pressure to remove solvent. The residue is purified by silica gel chromatography (solvent, ethyl acetate:chloroform=1:6). 1.97 g of 2-[3-(4-phenylpiperazin-1-yl)propylthio]benzaldehyde are obtained as an oil. Yield: 90.5%.

後処理

  1. stirringthe mixture is stirred at -50° C. for 5 minutes
  2. stirringfurther stirred at room temperature for one hour
  3. extractionthe aqueous mixture is extracted with methylene chloride
  4. washThe extract is washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customto remove solvent
  8. customThe residue is purified by silica gel chromatography (solvent, ethyl acetate:chloroform=1:6)

出典と根拠

ORDレコード
ord-e1eec7f7add74932a65c6586620a67b0
出典データセット
uspto-grants-1987_08
特許番号
US04689327

反応ノート

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