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

HRID 1921381ノート

反応式

HRID 1921381 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-06c66e66e4294e0b9a7f8638b20bc2a2
出典データセット
uspto-grants-2012_05
特許番号
US08173682B2

反応ノート

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