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

HRID 482523ノート

反応式

HRID 482523 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-289cd1e97bde4fcf80154f258749095b
出典データセット
uspto-grants-1998_08
特許番号
US05798375

反応ノート

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