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

HRID 384679

反応式

HRID 384679 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-a0fce03ae79e4e8882d8fa7ee697e6d1
出典データセット
uspto-grants-2013_02
特許番号
US08367658B2

関連ノート

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