Acetic Acid → 5-(4-Methoxycarbonylmethyloxybenzyl)thiazolidine-2,4-dione

HRID 1275066노트

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HRID 1275066 반응식
C(O)(=O)C.O.[CH3:6][O:7][C:8]([CH2:10][O:11][C:12]1[CH:44]=[CH:43][C:15]([CH2:16][CH:17]2[S:21][C:20](=[O:22])[N:19](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:18]2=[O:42])=[CH:14][CH:13]=1)=[O:9]>O1CCOCC1>[CH3:6][O:7][C:8]([CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][CH:17]2[S:21][C:20](=[O:22])[NH:19][C:18]2=[O:42])=[CH:43][CH:44]=1)=[O:9]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 962WaterHCID 221190505-(4-Methoxycarbonylmethoxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione

생성물 1

HCID 235141985-(4-Methoxycarbonylmethyloxybenzyl)thiazolidine-2,4-dione수율 85.6%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

1700 ml of acetic acid and then 400 ml of water were added at room temperature to a suspension of 344 g of 5-(4-methoxycarbonylmethoxybenzyl)-3-triphenylmethyl-thiazolidine-2,4-dione [prepared as described in step (f) above] in 400 ml of 1,4-dioxane and the resulting mixture was stirred for 5 hours at 80° C. At the end of this time, the reaction mixture was freed from the solvent by evaporation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel using a 1:2 by volume mixture of ethyl acetate and hexane, a 2:1 by volume mixture of ethyl acetate and hexane and then ethyl acetate as eluents, to give 161.7 g of the title compound, melting at 100-106° C.

후처리

  1. customAt the end of this time, the reaction mixture was freed from the solvent by evaporation under reduced pressure
  2. customthe resulting residue was purified by column chromatography through silica gel using a 1:2
  3. additionby volume mixture of ethyl acetate and hexane
  4. additiona 2:1 by volume mixture of ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-cf104ad2f4104ece9439c2e922c1429a
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06159997

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