Triethylamine → N-(2,6-dichloropyridin-4-yl)pivalamide

HRID 473316ノート

反応式

HRID 473316 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.C(N(CC)CC)C.[CH3:17][C:18]([CH3:23])([CH3:22])[C:19](Cl)=[O:20]>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:19](=[O:20])[C:18]([CH3:23])([CH3:22])[CH3:17])[CH:5]=[C:4]([Cl:9])[N:3]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 1376524-Amino-2,6-dichloropyridine

生成物 1

HCID 72942699N-(2,6-dichloropyridin-4-yl)pivalamide収率 76.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

2,6-Dichloro-4-pyridinamine (10 g, 61.3 mmol) (Aldrich) and triethylamine (10.69 ml, 77 mmol) were combined in dichloromethane (DCM) (75 ml) and cooled in an ice-bath. 2,2-dimethylpropanoyl chloride (8.30 ml, 67.5 mmol) (Aldrich) in DCM (15 ml) was added drop wise and the mixture stirred whilst allowing to warm up overnight producing a clear dark orange solution. LCMS showed good conversion to product. The solution was washed with water and sat. NaHCO3 (100 ml each), dried with Na2SO4, filtered and concentrated to yield a dark orange solid. The crude product was taken up in the minimum of DCM and applied to a 320 g Companion XL silica column and eluted with 0% EtOAc in cyclohexane for 2 CVs then 0-15% EtOAc in cyclohexane over 12 CVs then held at 15% for 2 CV. Appropriate fractions were combined and evaporated to give the title compound as a yellow solid (11.59 g).

後処理

  1. temperaturecooled in an ice-bath
  2. temperatureto warm up overnight
  3. customproducing a clear dark orange solution
  4. washThe solution was washed with water and sat. NaHCO3 (100 ml each)
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a dark orange solid
  9. washeluted with 0% EtOAc in cyclohexane for 2 CVs
  10. customevaporated

出典と根拠

ORDレコード
ord-955dd28129ce4ae2a1fd2003c95437cc
出典データセット
uspto-grants-2014_01
特許番号
US08633319B2

反応ノート

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