Sodium Hydroxide → 3-(2,3-Difluorophenyl)propanenitrile

HRID 2374729ノート

反応式

HRID 2374729 の反応式
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11](O)=O.C(Cl)(=O)C(Cl)=O.S(N)([NH2:23])(=O)=O.[OH-].[Na+]>ClCCl.CN(C=O)C>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]#[N:23]

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 82267SulfamideHCID 37993363-(2,3-difluorophenyl)propanoic Acid

生成物 1

HCID 184490163-(2,3-Difluorophenyl)propanenitrile収率 100.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3-(2,3-difluorophenyl)-propionic acid (A1) (6.83 g, 36 mmol) in anhydrous dichloromethane (50 ml) containing a few drops of DMF was added oxalyl chloride (6.4 ml, 73 mmol) at 0° C. under argon. The solution was stirred at ambient temperature for 2 h and the solvent removed in vacuo. The residue was dissolved in sulfolane (30 ml) and added to sulfamide (4.23 g, 44 mmol) and the mixture heated at 120° C. for 3 h. The brown solution was cooled, poured into 2M sodium hydroxide solution (300 ml) and extracted with ether. The combined extracts were washed with water, dried (MgSO4) and evaporated to give the title compound as a brown oil (6.04 g, 98%). 1H-NMR (CDCl3) δ 2.68 (2H, t), 3.04 (2H, t), 7.01-7.15 (3H, m).

後処理

  1. customthe solvent removed in vacuo
  2. dissolutionThe residue was dissolved in sulfolane (30 ml)
  3. temperaturethe mixture heated at 120° C. for 3 h
  4. temperatureThe brown solution was cooled
  5. extractionextracted with ether
  6. washThe combined extracts were washed with water
  7. dry with materialdried (MgSO4)
  8. customevaporated

出典と根拠

ORDレコード
ord-8fe9811955454e82aae33139ae192141
出典データセット
uspto-grants-2008_12
特許番号
US07462620B2

反応ノート

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