Water → Ethyl 5-(4-nitrophenyl)thiazole-2-carboxylate

HRID 1024428노트

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HRID 1024428 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH2:11][NH:12][C:13](=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:6][CH:5]=1)([O-:3])=[O:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1.O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.CCOC(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:30][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

참가 물질

7

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 87949Lawesson's reagentHCID 66572182Ethyl 2-(2-(4-nitrophenyl)-2-oxoethylamino)-2-oxoacetate2회

생성물 1

HCID 53404682Ethyl 5-(4-nitrophenyl)thiazole-2-carboxylate수율 73.5%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

A solution of Ethyl 2-(2-(4-nitrophenyl)-2-oxoethylamino)-2-oxoacetate (Intermediate 1, step C, 5 g) and Lawesson's reagent (7.22 g) in 1,4-Dioxane (100 ml) was refluxed for 2 hours. The reaction mixture was cooled, water was added and the mixture was neutralized with saturated solution of Na2CO3. This was followed by addition of EtOAc and then the layers were separated. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to get dark brown residue. The residue was chromatographed on silica gel in 0.5:9.5 EtOAc:CHCl3 to get dark yellow colored solid which was crystallized in CHCl3/pet ether to yield 3.65 g (73%) of the title compound. 1H NMR (CDCl3, 300 MHz): δ 8.33 (d, 2H), 8.3 (s, 1H), 7.83 (d, 2H), 4.54 (q, 2H), 1.49 (t, 3H); MS (ES+) m/z 279 (M+1).

후처리

  1. temperatureThe reaction mixture was cooled
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto get dark brown residue
  7. customThe residue was chromatographed on silica gel in 0.5:9.5 EtOAc
  8. customCHCl3 to get dark yellow colored solid which
  9. customwas crystallized in CHCl3/pet ether

출처 및 근거

ORD 기록
ord-768940d956a8419c9a984d241c5ef41d
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722901B2

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