Chlorosulfonic acid → 5-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-sulfonyl chloride

HRID 1921381노트

반응식

HRID 1921381 반응식
P(Cl)(Cl)(Cl)(Cl)Cl.[Cl:7][S:8]([OH:11])(=O)=[O:9].[CH2:12]([C:14]1[C:15](=[O:26])[NH:16][C:17]([CH3:25])=[C:18]([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1)[CH3:13]>C(Cl)(Cl)Cl>[CH2:12]([C:14]1[C:15](=[O:26])[NH:16][C:17]([CH3:25])=[C:18]([C:20]2[S:21][C:22]([S:8]([Cl:7])(=[O:11])=[O:9])=[CH:23][CH:24]=2)[CH:19]=1)[CH3:13]

참가 물질

5

반응물 3

HCID 24638Chlorosulfonic acidHCID 24819Phosphorus pentachlorideHCID 674922683-ethyl-6-methyl-5-thiophen-2-yl-1H-pyridin-2-one

생성물 1

HCID 866103525-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-sulfonyl chloride수율 97%

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
0 °C

실험 절차

Phosphorus pentachloride (4.67 g, 22.4 mmol) is placed in a three neck round bottom flask and cooled to 0° C. Chlorosulfonic acid (6.53 g, 56.0 mmol) is added slowly. The reaction is stirred until the fuming action stops and the reaction mixture becomes clear. Then a solution of 3-ethyl-6-methyl-5-(thiophen-2-yl)-1H-pyridin-2-one (4.92 g, 22.4 mmol) of the above reaction in chloroform (35 mL) is added dropwise, and stirring at 0° C. is maintained for 5 min, then at room temperature. After 30 min, the reaction is poured into ice water (200 mL) and extracted with dichloromethane. The organic layer is washed with water, dried (sodium sulfate), filtered and concentrated and the residue is triturated with hepatane-30% ethyl acetate to afford the title compound (6.88 g, 97% yield) as a yellow solid. MS: m/e=318 (M+H). 1H-NMR (D6-DMSO, δ ppm) 13.2 (br s, 1H); 7.25 (s, 1H); 7.05 (d, 1H, J=3.2 Hz); 6.82 (d, 1H, J=3.2 Hz); 2.39 (q, 2H, J=7.4 Hz); 2.27 (s, 3H); 1.10 (t, 3H, J=7.4 Hz).

후처리

  1. additionis added dropwise
  2. stirringstirring at 0° C.
  3. temperatureis maintained for 5 min
  4. customat room temperature
  5. extractionextracted with dichloromethane
  6. washThe organic layer is washed with water
  7. dry with materialdried (sodium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customthe residue is triturated with hepatane-30% ethyl acetate

출처 및 근거

ORD 기록
ord-06c66e66e4294e0b9a7f8638b20bc2a2
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173682B2

반응 노트

불러오는 중…