Sulfuric Acid → 5-[4-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-2,4-thiazolidinedione

HRID 4389노트

반응식

HRID 4389 반응식
N=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[N:18]=[C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[O:20][C:21]=3[CH3:22])=[CH:11][CH:10]=2)[S:3]1.[OH:29]S(O)(=O)=O.O1CCOCC1>O>[CH3:22][C:21]1[O:20][C:19]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[N:18][C:17]=1[CH2:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH:4]2[S:3][C:2](=[O:29])[NH:6][C:5]2=[O:7])=[CH:10][CH:11]=1

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 312751,4-DioxaneHCID 140348400HCID 140348400, 화합물

생성물 1

HCID 137138985-[4-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-2,4-thiazolidinedione수율 58.8%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 2-imino-5-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-4-thiazolidinone (11.4 g), 1N.H2SO4 (100 ml) and dioxane (100 ml) was stirred at 80° C. for 5 hours, and poured in water. The aqueous mixture was extracted with chloroform. The chloroform layer was washed with water, dried (MgSO4) and concentrated. The oily residue was chromatographed on a column of silica gel (200 g), and from the fractions eluted with chlorform-methanol (100:1, V/V), there was obtained 5-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-2,4-thiazolidinedione (6.7 g, 58.8%). Recrystallization from ethyl acetate-hexane afforded colorless plates. m.p. 162°-163° C. Elemental analysis for C21H18N2O4S, Calcd.: C, 63.95; H, 4.60; N, 7.10. Found: C, 63.84; H, 4.63; N, 6.90. This product showed the IR and NMR spectra in accordance with those of the compound obtained in Example 6.

후처리

  1. extractionThe aqueous mixture was extracted with chloroform
  2. washThe chloroform layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe oily residue was chromatographed on a column of silica gel (200 g)
  6. washfrom the fractions eluted with chlorform-methanol (100:1, V/V)

출처 및 근거

ORD 기록
ord-8b6234674c5d40d897dae8a634dc35f0
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725610

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