Hydrochloric Acid → 5-[4-(4-Chlorobenzyloxy)benzyl]thiazolidine-2,4-dione

HRID 326161

反応式

HRID 326161 の反応式
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH:7]2[S:11][C:10](=[O:12])[NH:9][C:8]2=[O:13])=[CH:4][CH:3]=1.[H-].[Na+].[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1.Cl>O.CS(C)=O>[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][O:1][C:2]2[CH:15]=[CH:14][C:5]([CH2:6][CH:7]3[S:11][C:10](=[O:12])[NH:9][C:8]3=[O:13])=[CH:4][CH:3]=2)=[CH:21][CH:20]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 101983975-(4-Hydroxybenzyl)thiazolidine-2,4-dione

生成物 1

HCID 129441795-[4-(4-Chlorobenzyloxy)benzyl]thiazolidine-2,4-dione収率 24.4%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

To 12 ml of dimethylsulfoxide is dissolved 1.12 g of 5-(4-hydroxybenzyl)thiazolidine-2,4-dione, and 480 mg of 50% sodium hydride in oil is added to the solution. The mixture is stirred at room temperature for 15 minutes, to which is added 0.81 g of 4-chlorobenzyl chloride. The whole mixture is stirred at 50° C. for 4 hours. Water is added to the mixture and the mixture is acidified with 2 N-hydrochloric acid. The mixture is subjected to extraction with ether. The extract is washed with water and dried. Ether is distilled off to give an oily substance. The oily substance is subjected to column chromatography on 30 g silica gel, elution being carried out with cyclohexane-ethyl acetate (2:1). By the above procedure there was obtained 425 mg of 5-[4-(4-chlorobenzyloxy)benzyl]thiazolidine-2,4-dione.

後処理

  1. additionis added to the solution
  2. stirringThe whole mixture is stirred at 50° C. for 4 hours
  3. extractionThe mixture is subjected to extraction with ether
  4. washThe extract is washed with water
  5. customdried
  6. distillationEther is distilled off
  7. customto give an oily substance
  8. washThe oily substance is subjected to column chromatography on 30 g silica gel, elution

出典と根拠

ORDレコード
ord-d746099267f04dc89331f624dc72fad8
出典データセット
uspto-grants-1984_04
特許番号
US04444779

関連ノート

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