Dimethylformamide → N,5-Dimethyl-3-phenyl-4-isoxazolecarboxamide

HRID 8307

反応式

HRID 8307 の反応式
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]([OH:15])=O.[CH3:16][N:17](C)C=O.S(Cl)(Cl)=O.CN>ClCCCl.C(O)C>[CH3:16][NH:17][C:13]([C:3]1[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][O:6][C:2]=1[CH3:1])=[O:15]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 6329MethylamineHCID 143435-Methyl-3-phenylisoxazole-4-carboxylic acidHCID 24386Thionyl Chloride

生成物 1

HCID 4104650N,5-Dimethyl-3-phenyl-4-isoxazolecarboxamide

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 50.0 g (0.25 mol) of 5-methyl-3-phenyl-isoxazole-4-carboxylic acid in 1.2 l of 1,2-dichloroethane (DCE) is added 1.9 ml dimethyl formamide (DMF) and 21.4 ml (0.3 mol, 1.2 eq.) of thionyl chloride. The mixture is stirred for 2 h at reflux until a clear, yellow solution is formed. The solution is cooled to room temperature and then slowly added to a 8M solution of methylamine in ethanol (146 ml) at 5° C. The suspension is poured onto methylene chloride, washed with sat. NaHCO3-solution, dried over Na2SO4 and concentrated. This yields 52.3 g (99%) of the title compound as light brown solid, which is used for further reaction without purification. Mass spectrum: m/z (M+H)+: 217.1

後処理

  1. temperatureat reflux until a clear, yellow 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 52.3 g (99%) of the title compound as light brown solid, which is used for further reaction without purification

出典と根拠

ORDレコード
ord-9f2d7503c50f422082db2b1fd2579b77
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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