Chloroacetyl chloride → 2-Chloro-N-(3-fluoro-pyridin-4-yl)-acetamide

HRID 2192386노트

반응식

HRID 2192386 반응식
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH2:8].C(N(CC)CC)C.[Cl:16][CH2:17][C:18](Cl)=[O:19]>ClCCl>[Cl:16][CH2:17][C:18]([NH:8][C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[F:1])=[O:19]

참가 물질

5

반응물 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 8171224-Amino-3-fluoropyridine

생성물 1

HCID 595037592-Chloro-N-(3-fluoro-pyridin-4-yl)-acetamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 3-fluoro-pyridin-4-ylamine (0.2 g) in dry dichloromethane (2 mL) under nitrogen at 0° C. was treated with triethylamine (0.28 mL) followed by slow addition of chloroacetyl chloride (0.16 mL). The reaction mixture was allowed to warm up to room temperature. After 2 h, the mixture was partitioned between dichloromethane and water The phases were separated and the aqueous layer was extracted with dichloromethane (×2). The combined organic layer was washed with brine, dried over sodium sulphate, filtered and concentrated to give the crude product which was purified by silica gel chromatography eluting with 0-100% EtOAc/cyclohexane. The relevant fractions were combined and evaporated to give the title compound (0.11 g) as a pink solid.

후처리

  1. customthe mixture was partitioned between dichloromethane and water The phases
  2. customwere separated
  3. extractionthe aqueous layer was extracted with dichloromethane (×2)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product which
  9. customwas purified by silica gel chromatography
  10. washeluting with 0-100% EtOAc/cyclohexane
  11. customevaporated

출처 및 근거

ORD 기록
ord-ae5256a72c1b4a959f450ab91dcab968
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329729B2

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