Cesium carbonate → 5-(4-Methoxycarbonylmethoxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione

HRID 1419117노트

반응식

HRID 1419117 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[CH:40]=[CH:39][C:11]([CH2:12][CH:13]2[S:17][C:16](=[O:18])[N:15]([C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]2=[O:38])=[CH:10][CH:9]=1.Br[CH2:42][C:43]([O:45][CH3:46])=[O:44]>CC(C)=O>[CH3:46][O:45][C:43]([CH2:42][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][CH:13]2[S:17][C:16](=[O:18])[N:15]([C:19]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:14]2=[O:38])=[CH:39][CH:40]=1)=[O:44]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 28181265-(4-Hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione

생성물 1

HCID 221190505-(4-Methoxycarbonylmethoxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

126 g of cesium carbonate were added at room temperature to a solution of 120 g of 5-(4-hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione in 2.5 liters of acetone, followed by 36 ml of methyl bromoacetate, and the resulting mixture was stirred for 1 hour. At the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure, and the resulting residue was mixed with water. The aqueous mixture was then extracted with ethyl acetate. The extract was washed with water and then with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, after which 1 liter of diethyl ether was added to the oily residue. The mixture was then agitated ultrasonically for 10 minutes. The solid substance precipitated was collected by filtration, to give 126.3 g of the title compound, melting at 158°-162° C.

후처리

  1. distillationAt the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure
  2. additionthe resulting residue was mixed with water
  3. extractionThe aqueous mixture was then extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialwith a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. additionafter which 1 liter of diethyl ether was added to the oily residue
  8. stirringThe mixture was then agitated ultrasonically for 10 minutes
  9. customThe solid substance precipitated
  10. filtrationwas collected by filtration

출처 및 근거

ORD 기록
ord-1615a0c5d75c4669b31d1a78c22bcc12
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05886014

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