Sodium Chloride → Ethyl (1,3-thiazol-2-yl)acetate

HRID 218231

반응식

HRID 218231 반응식
[S:1]1[CH:5]=[CH:4][NH:3][C:2]1=[C:6](C(OCC)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Cl-].[Na+]>CS(C)=O.O>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]

참가 물질

5

반응물 2

HCID 5234Sodium ChlorideHCID 10977652Diethyl 2-(thiazol-2(3H)-ylidene)malonate

생성물 1

HCID 21835228Ethyl (1,3-thiazol-2-yl)acetate

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매2회

실험 절차

A solution of the product of Example 44B (2.8 g, 11.5 mmoles), sodium chloride (1.3 g, 22.9 mmoles) and water (0.4 ml, 22.9 mmoles) in dimethyl sulfoxide (48.0 ml) was stirred at about 180° C. for about 30 min. The mixture was cooled, diluted with water (100.0 ml) and was extracted twice with (1:1) ethyl acetate/diethyl ether (80.0 ml each). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuum. The crude product was purified by flash column chromatography on silica gel using hexanes/ethyl acetate (2:1) as the mobile phase to provide the title compound.

후처리

  1. temperatureThe mixture was cooled
  2. extractionwas extracted twice with (1:1) ethyl acetate/diethyl ether (80.0 ml each)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customThe crude product was purified by flash column chromatography on silica gel

출처 및 근거

ORD 기록
ord-ae3ff4bad61642ed90f38fc3b7507639
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198331B2

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