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

HRID 1027697ノート

反応式

HRID 1027697 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 590004705-chloro-N,N-dimethylpyrazine-2-carboxamide収率 100.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-5aa1f562001546f6b62359321c919f0f
出典データセット
uspto-grants-2014_05
特許番号
US08735396B2

反応ノート

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