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

HRID 2374729노트

반응식

HRID 2374729 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 184490163-(2,3-Difluorophenyl)propanenitrile수율 100.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8fe9811955454e82aae33139ae192141
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07462620B2

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