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Methyl vinyl sulfone → 5-Bromo-1-[2-(methylsulfonyl)ethyl]pyridin-2(1H)-one

HRID 869907
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HRID 869907 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.[CH3:9][S:10]([CH:13]=[CH2:14])(=[O:12])=[O:11]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([CH2:14][CH2:13][S:10]([CH3:9])(=[O:12])=[O:11])[CH:7]=1
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참가 물질

4

반응물 2

HCID 19354Methyl vinyl sulfoneHCID 178515818HCID 178515818, 화합물

생성물 1

HCID 607465825-Bromo-1-[2-(methylsulfonyl)ethyl]pyridin-2(1H)-one수율 29%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

5-Bromopyridin-2-ol (4.0 g, 23.0 mmol) and methylsulfonylethene (2.4 g, 2.0 mL, 23.0 mmol) were combined in N,N-dimethylformamide (DMF, 23 mL) and heated to 100° C. The crude reaction mixture was then evaporated to dryness. The crude material was then dissolved in a minimum of dichloromethane. The solution was then washed twice with an aqueous 1 M solution of hydrochloric acid, two times with a saturated aqueous solution of sodium bicarbonate, two times with a saturated aqueous solution of sodium chloride, and finally by two washes of water. The organic layer was dried over sodium sulfate and then evaporated to dryness to yield the product as a pale brown solid (1.87 g, 6.68 mmol, 29%). ESI-MS m/z calc. 279.0. found 280.0 (M+1)+. Retention time 0.34 minutes.

후처리

  1. customThe crude reaction mixture
  2. customwas then evaporated to dryness
  3. dissolutionThe crude material was then dissolved in a minimum of dichloromethane
  4. washThe solution was then washed twice with an aqueous 1 M solution of hydrochloric acid, two times with a saturated aqueous solution of sodium bicarbonate, two times with a saturated aqueous solution of sodium chloride
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customevaporated to dryness

출처 및 근거

ORD 기록
ord-b8fb998449f846128933bcb6ed9cc48d
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08969386B2

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