Triethylamine → HCID 25102948、化合物

HRID 906689ノート

反応式

HRID 906689 の反応式
[O:1]1[CH2:6][CH2:5][CH:4]=[CH:3][C:2]1=[O:7].[CH2:8]([N:10](CC)CC)C.[N:15]1[O:16][N:17]=[C:18]2[CH:23]=[C:22]([C:24](Cl)=[O:25])[CH:21]=[CH:20][C:19]=12>CN.C(O)C.ClCCl>[CH3:8][N:10]([CH:4]1[CH2:5][CH2:6][O:1][C:2](=[O:7])[CH2:3]1)[C:24]([C:22]1[CH:21]=[CH:20][C:19]2=[N:15][O:16][N:17]=[C:18]2[CH:23]=1)=[O:25]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 5206605,6-Dihydro-2H-pyran-2-oneHCID 27354532,1,3-Benzoxadiazole-5-carbonyl chloride

生成物 1

HCID 25102948HCID 25102948、化合物

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 6329Methylamine溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
55 °C

実験手順

5,6-Dihydro-2H-pyran-2-one (1.0 g, 10.2 mmol) was dissolved in 3 ml of a 33% solution of methylamine in ethanol and heated to 55° C. overnight. The solvent was evaporated, the residue dissolved in methanol (20 ml) and conc. HCl (20 ml) and the mixture heated at 95° C. for 2.5 h. The mixture was evaporated to dryness, the residue dissolved in THF (20 ml), dichloromethane (20 ml) and triethylamine (3 ml) and a solution of [2,1,3]-benzoxadiazole-5-carboxylic acid chloride (2.0 g, 11 mmol), in dichloromethane (5 ml), added. After stirring is the mixture for 0.75 h, the mixture was washed with 1N HCl and conc. NaHCO3 solution, dried over sodium sulfate, and concentrated under vacuum. The residue was purified on a silica gel column using ethyl acetate/hexane/dichloromethane (70:20:10), to give N-methyl-N-(2-oxotetrahydro-2H-pyran-4-yl)-[2,1,3]-benzoxadiazole-5-carboxamide as white solid after crystallization from dichloromethane/methanol (0.21 g). Mp=169-171° C., 1H NMR (300 MHz, CDCl3, rotamers) δ 7.97 (d, J=9.0 Hz, 1H); 7.90 (s, 1H); 7.40 (d, J=9.0 Hz, 1H); 5.10-4.40 (m, 3H); 3.01 (s, 3H); 3.00-2.74 (m, 2H) and 2.60-2.10 ppm (s, 2H).

後処理

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in methanol (20 ml)
  3. temperatureconc. HCl (20 ml) and the mixture heated at 95° C. for 2.5 h
  4. customThe mixture was evaporated to dryness
  5. dissolutionthe residue dissolved in THF (20 ml)
  6. customfor 0.75 h
  7. washthe mixture was washed with 1N HCl and conc. NaHCO3 solution
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified on a silica gel column

出典と根拠

ORDレコード
ord-39d354f2c0c143868e9d8d20aba893cd
出典データセット
uspto-grants-2011_09
特許番号
US08013003B2

反応ノート

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