Formamide → 5-Oxazol-4-yl-thiophene-3-carboxylic acid methyl ester

HRID 1914593

반응식

HRID 1914593 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10](=O)[CH2:11]Br)[S:7][CH:6]=1)=[O:4].S(=O)(=O)(O)O.[CH:19]([NH2:21])=[O:20]>>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[N:21]=[CH:19][O:20][CH:11]=2)[S:7][CH:6]=1)=[O:4]

참가 물질

4

반응물 3

HCID 713FormamideHCID 1118Sulfuric AcidHCID 539045465-(2-Bromo-acetyl)-thiophene-3-carboxylic acid methyl ester

생성물 1

HCID 581102445-Oxazol-4-yl-thiophene-3-carboxylic acid methyl ester

반응 조건

온도
150 °C

실험 절차

5-(2-Bromo-acetyl)-thiophene-3-carboxylic acid methyl ester (0.60 g, 2.28 mmol) was suspended in formamide (10 mL) then sulfuric acid (1 mL) was added and the tube purged with nitrogen then sealed. The mixture was heated at 150° C. by microwave irradiation for 15 minutes. The resultant solution was diluted with HCl (1 N) and water and extracted with ethyl acetate (×3). The organic phase was dried over sodium sulfate and evaporated then purified by chromatography on a silica II cartridge, eluting with 1:1 DCM:cyclohexane to afford 5-oxazol-4-yl-thiophene-3-carboxylic acid methyl ester as a pale yellow solid (0.197 g). LCMS m/z 210.14 [M+H]+ R. T.=3.64 min (Analytical Method 9).

후처리

  1. customthe tube purged with nitrogen
  2. customthen sealed
  3. additionThe resultant solution was diluted with HCl (1 N) and water
  4. extractionextracted with ethyl acetate (×3)
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customevaporated
  7. customthen purified by chromatography on a silica II cartridge
  8. washeluting with 1:1 DCM

출처 및 근거

ORD 기록
ord-81f9109593554d81b4f5f8e543e1fb83
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614209B2

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