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Acetic Acid → N-(2-(6-chloropyridin-3-yl)propan-2-yl)acetamide

HRID 449550
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HRID 449550 반응식
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8](O)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[C:12]([OH:15])(=O)[CH3:13].C(#[N:18])C>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([NH:18][C:12](=[O:15])[CH3:13])([CH3:10])[CH3:9])=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 3

HCID 176Acetic AcidHCID 6342AcetonitrileHCID 125621182-(6-Chloropyridin-3-yl)propan-2-ol

생성물 1

HCID 77231171N-(2-(6-chloropyridin-3-yl)propan-2-yl)acetamide

실험 절차

2-(6-chloropyridin-3-yl)propan-2-ol (637 mg, 3.71 mmol, Eq: 1.00) was dissolved in acetonitrile (5 ml). Acetic acid (2.9 g, 2.76 ml, 48.3 mmol, Eq: 13) was added at room temperature and cooled after the addition to 0° C. Sulfuric acid, concentrated (5.1 g, 2.77 ml, 52.0 mmol, Eq: 14) was added dropwise to the solution, then allowed to warm up to room temperature and stirred over night. The reaction mixture was poured into ice, concentrated NaOH solution was added until pH was basic; extracted with ethyl acetate; org. phase was washed with brine; dried with sodium sulfate; filtered to give a yellow solid. This residue was triturated with ethyl acetate and a little bit hexane. Resulting precipitate was filtered off to give a white solid (338 mg, 1.59 mmol).

후처리

  1. temperaturecooled
  2. additionafter the addition to 0° C
  3. concentrationSulfuric acid, concentrated (5.1 g, 2.77 ml, 52.0 mmol, Eq: 14)
  4. additionwas added dropwise to the solution
  5. additionThe reaction mixture was poured into ice, concentrated NaOH solution
  6. additionwas added until pH
  7. extractionextracted with ethyl acetate
  8. washphase was washed with brine
  9. dry with materialdried with sodium sulfate
  10. filtrationfiltered
  11. customto give a yellow solid
  12. customThis residue was triturated with ethyl acetate
  13. customResulting precipitate
  14. filtrationwas filtered off

출처 및 근거

ORD 기록
ord-d7d080f74fd141f6b36046583aa75204
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08481540B2

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