Chlorosuccinimide → N-(4,5-Dichloropyridin-2-yl)pivalamide

HRID 384675노트

반응식

HRID 384675 반응식
C1C(=O)N([Cl:8])C(=O)C1.[Cl:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH:11]=1>C(#N)C>[Cl:9][C:10]1[C:15]([Cl:8])=[CH:14][N:13]=[C:12]([NH:16][C:17](=[O:22])[C:18]([CH3:19])([CH3:21])[CH3:20])[CH:11]=1

참가 물질

4

반응물 2

HCID 31398ChlorosuccinimideHCID 10656204N-(4-Chloropyridin-2-yl)pivalamide

생성물 1

HCID 10538422N-(4,5-Dichloropyridin-2-yl)pivalamide수율 75%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

NCS (3.14 g. 23.5 mmol) was added to a solution of N-(4-chloropyridin-2-yl)pivalamide (1.00 g, 4.7 mmol) in dry acetonitrile (10 mL). The resulting suspension was heated for 3 h and then cooled to r.t. The solvent was removed in vacuo and the crude mixture was diluted with ethyl acetate (50 mL). The organic phase was washed with aqueous NaOH (10%, 2×20 mL), water (20 mL) and dried (MgSO4). The solvent was removed in vacuo and the crude mixture was purified by flash chromatography on silica, eluting with ethyl acetate and hexane (1/9), to give the title compound as a colourless solid (0.87 g, 75%).

후처리

  1. temperatureThe resulting suspension was heated for 3 h
  2. customThe solvent was removed in vacuo
  3. additionthe crude mixture was diluted with ethyl acetate (50 mL)
  4. washThe organic phase was washed with aqueous NaOH (10%, 2×20 mL), water (20 mL)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customthe crude mixture was purified by flash chromatography on silica
  8. washeluting with ethyl acetate and hexane (1/9)

출처 및 근거

ORD 기록
ord-695609b69ed944b090847712fcf74d93
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367658B2

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