Triethylamine → 5-chloro-N,N-dimethylpyrazine-2-carboxamide

HRID 1027697

반응식

HRID 1027697 반응식
[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8](Cl)=[O:9])=[N:6][CH:7]=1.Cl.[CH3:12][NH:13][CH3:14].C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([N:13]([CH3:14])[CH3:12])=[O:9])=[N:6][CH:7]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 152157435-Chloropyrazine-2-carbonyl chloride

생성물 1

HCID 590004705-chloro-N,N-dimethylpyrazine-2-carboxamide수율 100.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

5-chloropyrazine-2-carbonyl chloride (2.13 gram, 12.05 mmol) and dimethylamine HCl salt (1.06 gram, 12.7 mmol) were suspended in dichloromethane (50 mL) with stirring. Triethylamine (5.04 mL, 36.2 mmol) in dichloromethane (25 mL) was added dropwise at 0° C. to the reaction mixture. The combined solution was warmed up to ambient temperature and stirred for 4 hours. The compound was diluted with dichloromethane, washed with 1N HCl, water, brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by column chromatography (silica gel, gradient of 30 to 80% ethyl acetate in heptane) to provide desired 5-chloro-N,N-dimethylpyrazine-2-carboxamide (SM-1: 2.24 g, 85%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.74 (d, J=1.37 Hz, 1H) 8.53 (d, J=1.37 Hz, 1H) 3.15 (s, 3H) 3.12 (s, 3H)

후처리

  1. stirringstirred for 4 hours
  2. washwashed with 1N HCl, water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (silica gel, gradient of 30 to 80% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-5aa1f562001546f6b62359321c919f0f
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735396B2

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