N-bromobutanimide → N-(5-bromo-4-chloropyridin-2-yl)-2,2-dimethylpropanamide

HRID 556841

반응식

HRID 556841 반응식
C1C(=O)N([Br:8])C(=O)C1.[Cl:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH:11]=1>C(#N)C>[Br:8][C:15]1[C:10]([Cl:9])=[CH:11][C:12]([NH:16][C:17](=[O:22])[C:18]([CH3:19])([CH3:21])[CH3:20])=[N:13][CH:14]=1

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 10656204N-(4-Chloropyridin-2-yl)pivalamide

생성물 1

HCID 59613421N-(5-bromo-4-chloropyridin-2-yl)-2,2-dimethylpropanamide수율 66.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

NBS (8.37 g. 47.0 mmol) was added to a solution of N-(4-chloropyridin-2-yl)pivalamide (2.00 g, 9.40 mmol) in dry acetonitrile (20 mL). The resulting suspension was heated for 3 hr and then cooled to r.t. The solvent was removed in vacuo and the crude mixture was diluted with ethyl acetate (100 mL). The organic phase was washed with aqueous NaOH (10%, 2×40 mL), water (40 mL) and dried (MgSO4). The solvent was removed in vacuo and the crude mixture was purified by flash chromatography on silica, eluting with ethyl acetate and hexane (1/9), to give the title compound as a colourless solid (1.82 g, 66%).

후처리

  1. temperatureThe resulting suspension was heated for 3 hr
  2. customThe solvent was removed in vacuo
  3. additionthe crude mixture was diluted with ethyl acetate (100 mL)
  4. washThe organic phase was washed with aqueous NaOH (10%, 2×40 mL), water (40 mL)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customthe crude mixture was purified by flash chromatography on silica
  8. washeluting with ethyl acetate and hexane (1/9)

출처 및 근거

ORD 기록
ord-bc15ec3f196e42aeaa0742554446ad00
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058045B2

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