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

HRID 1759343

반응식

HRID 1759343 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9350b796de31433aa1aff9e985c5ceb5
출처 데이터셋
uspto-grants-1982_07
특허 번호
US04340605

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