Hydrochloric Acid → 5-[4-(5-Methoxy-1-methylbenzimidazol-2-ylmethoxy)benzyl]thiazolidine-2,4-dione

HRID 1419100노트

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HRID 1419100 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH3:10])=[C:5]([NH2:11])[CH:4]=1.CO[C:14]([CH2:16][O:17][C:18]1[CH:31]=[CH:30][C:21]([CH2:22][CH:23]2[S:27][C:26](=[O:28])[NH:25][C:24]2=[O:29])=[CH:20][CH:19]=1)=O.Cl.C(=O)([O-])O.[Na+]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[N:9]([CH3:10])[C:14]([CH2:16][O:17][C:18]3[CH:19]=[CH:20][C:21]([CH2:22][CH:23]4[S:27][C:26](=[O:28])[NH:25][C:24]4=[O:29])=[CH:30][CH:31]=3)=[N:11][C:5]=2[CH:4]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 45184444-methoxy-1-N-methylbenzene-1,2-diamineHCID 235141985-(4-Methoxycarbonylmethyloxybenzyl)thiazolidine-2,4-dione

생성물 1

HCID 99526545-[4-(5-Methoxy-1-methylbenzimidazol-2-ylmethoxy)benzyl]thiazolidine-2,4-dione수율 9.8%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A mixture of 1.17 g of 4-methoxy-N-methyl-1,2-phenylenediamine (prepared as described in Preparation 25), 3.0 g of 5-(4-methoxycarbonylmethoxybenzyl)thiazolidine-2,4-dione (prepared as described in Preparation 21), 20 ml of 1,4-dioxane and 60 ml of concentrated hydrochloric acid was heated under reflux for 2 days. At the end of this time, the reaction mixture was poured into ice-water and the resulting mixture was neutralized with sodium hydrogencarbonate, after which it was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, after which the residue was purified by column chromatography through silica gel, using a solution of methylene chloride containing 3% by volume ethanol as the eluent, to give 0.3 g of the title compound, melting at 209°-210° C. and having an Rf value=0.56 (on thin layer chromatography on silica gel; developing solvent: methylene chloride containing 5% by volume ethanol).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 2 days
  3. extractionafter which it was extracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was then removed by distillation under reduced pressure
  7. customafter which the residue was purified by column chromatography through silica gel

출처 및 근거

ORD 기록
ord-21c1ab9642f7414784f95012bbc2f704
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05886014

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