Water → 5-Ethyl-2-thiophenecarboxylic acid, N-t-butyl amide

HRID 235083

반응식

HRID 235083 반응식
[CH2:1]([C:3]1[S:7][C:6]([C:8]([OH:10])=O)=[CH:5][CH:4]=1)[CH3:2].S(Cl)(Cl)=O.[C:15]([NH2:19])([CH3:18])([CH3:17])[CH3:16].O>C(Cl)Cl.CCCCCC>[C:15]([NH:19][C:8]([C:6]1[S:7][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=1)=[O:10])([CH3:18])([CH3:17])[CH3:16]

참가 물질

7

반응물 4

HCID 962WaterHCID 6385Tert-ButylamineHCID 24386Thionyl ChlorideHCID 5881925-Ethylthiophene-2-carboxylic acid

생성물 1

HCID 606993245-Ethyl-2-thiophenecarboxylic acid, N-t-butyl amide수율 80%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8058Hexane용매

반응 조건

온도
0 °C

실험 절차

To a solution of 28 g (0.18 mol) of 5-ethyl-2-thiophenecarboxylic acid, from step 3a above, in 130 mL of methylene chloride was added a large excess (130 mL, 10 mol) of thionyl chloride, and the solution was heated at reflux for 2 hours. The solvent and excess reagent were removed by evaporation, and the residue was dissolved in 130 mL of chloroform and cooled to 0° C. To this solution was added 94 mL (0.9 mol) of t-butylamine dropwise, and the solution was stirred at reflux for 2 hours. The reaction was cooled, the solution poured into water, and the mixture extracted with ethyl acetate. The extract was washed with water and brine, dried, and concentrated. The residue was dissolved in ethyl acetate and the crude product was precipitated by addition of hexane. The crude product was collected by filtration and purified by flash chromatography over silica gel, eluting with 1:6 ethyl acetate:hexane, to afford 13.3 g (80% yield) of the title product after drying. MS 212 (M+H)+. NMR (CDCl3) δ: 7.25 (d, 1H, J=3 Hz), 6,72 (d, 1H, J=3 Hz), 5.70 (bs, 1H), 2.84 (q, 2H, J=7 Hz), 1.45 (s, 9H), 1.31 (t, 3H, J=7 Hz).

후처리

  1. temperaturethe solution was heated
  2. temperatureat reflux for 2 hours
  3. customThe solvent and excess reagent were removed by evaporation
  4. dissolutionthe residue was dissolved in 130 mL of chloroform
  5. temperatureat reflux for 2 hours
  6. temperatureThe reaction was cooled
  7. extractionthe mixture extracted with ethyl acetate
  8. washThe extract was washed with water and brine
  9. customdried
  10. concentrationconcentrated
  11. dissolutionThe residue was dissolved in ethyl acetate
  12. customthe crude product was precipitated by addition of hexane
  13. filtrationThe crude product was collected by filtration
  14. custompurified by flash chromatography over silica gel
  15. washeluting with 1:6 ethyl acetate

출처 및 근거

ORD 기록
ord-23b6fc38c21d44bf962b28e9020bf8fb
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05597832

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