Dimethylformamide → 3-Methyl-5-phenyl-isoxazole-4-carboxylic acid methylamide

HRID 8309

反応式

HRID 8309 の反応式
[CH3:1][C:2]1[C:6]([C:7](O)=[O:8])=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:4][N:3]=1.[CH3:16][N:17](C=O)C.S(Cl)(Cl)=O.CN>ClCCCl.C(O)C>[CH3:16][NH:17][C:7]([C:6]1[C:2]([CH3:1])=[N:3][O:4][C:5]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:8]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 6329MethylamineHCID 24386Thionyl ChlorideHCID 27765143-Methyl-5-phenylisoxazole-4-carboxylic acid

生成物 1

HCID 666631943-Methyl-5-phenyl-isoxazole-4-carboxylic acid methylamide

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 702Ethanol溶媒

実験手順

To a suspension of 6.0 g (29.6 mmol) of 3-methyl-5-phenyl-isoxazole-4-carboxylic acid in 150 ml DCE is added 0.3 ml of DMF and 2.6 ml (35.5 mmol, 1.2 eq.) of thionyl chloride. The mixture is stirred for 2 h at reflux until a brown solution is formed. The solution is cooled to room temperature and then slowly added to a 8M solution of methylamine in ethanol (18 ml) at 5° C. The suspension is poured onto methylene chloride, washed with sat. NaHCO3-solution, dried over Na2SO4 and concentrated. This yields 6.7 g (quant.) of the title compound as brown solid, which is used for further reactions without purification. Mass spectrum: m/z (M+H)+: 217.2

後処理

  1. temperatureat reflux until a brown solution
  2. customis formed
  3. additionThe suspension is poured onto methylene chloride
  4. washwashed with sat. NaHCO3-solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThis yields 6.7 g (quant.) of the title compound as brown solid, which is used for further reactions without purification

出典と根拠

ORDレコード
ord-a28927d749e14940b77d1c3cd041bd45
出典データセット
uspto-grants-2006_08
特許番号
US07087756B2

関連ノート

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