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Acetic Acid → Troglitazone

HRID 1940681
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HRID 1940681 반응식
[OH:1][C:2]1[C:3]([CH3:31])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]3[S:26][C:25](=N)[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=1)([CH3:14])[CH2:6][CH2:5]2.C(O)(=[O:34])C.Cl.C(=O)(O)[O-].[Na+]>O>[OH:1][C:2]1[C:3]([CH3:31])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:34])[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=1)([CH3:14])[CH2:6][CH2:5]2
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참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 1403415895-[[4-[(6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)methoxy]phenyl]methyl]-2-imino-1,3-thiazolidin-4-one

생성물 1

HCID 5591Troglitazone

시약·촉매·용매 1

HCID 962
Water
용매

실험 절차

15.5 g of 5-[4-(6-hydroxy-2,5,7, 8-tetramethyl chroman-2-yl-methoxy) benzyl]-2-iminothiazolidine-4-one, prepared by the process as described in Example-1, was added to a mixture of 225 ml of acetic acid, 75 ml of conc. hydrochloric acid and 40 ml of water and the mixture was refluxed for 12 hrs. The reaction mixture was cooled to room temperature and 66.2 g of sodium bicarbonate was added and once the evolution of carbondioxide had ceased, the solvent was distilled off applying high vacuum. A 10:1 by volume mixture of benzene and ethyl acetate was added to the residue and the erode product was washed with a mixture of equal volumes of a saturated aq. sodium bicarbonate solution & water. The organic layer was dried over anhydrous sodium sulphate and the solvent was distilled off The resulting crude product was quickly eluted from a silica gel column with 50% ethylacetate-hexane to furnish 12.5 g of the required 5-{4-(6-hydroxy-2, 5, 7, 8-tetramethylchroman-2-yl-methoxy) benzyl) thiazolidine-2,4-dione (Troglitazone) with a HPLC purity of ~67-70%.

후처리

  1. temperaturethe mixture was refluxed for 12 hrs
  2. distillationthe solvent was distilled off
  3. additionA 10:1 by volume mixture of benzene and ethyl acetate
  4. additionwas added to the residue
  5. washthe erode product was washed with a mixture of equal volumes of a saturated aq. sodium bicarbonate solution & water
  6. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  7. distillationthe solvent was distilled off The resulting crude product
  8. washwas quickly eluted from a silica gel column with 50% ethylacetate-hexane

출처 및 근거

ORD 기록
ord-c7ad814035844171b53c0bac892f4643
출처 데이터셋
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05700820

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