N-methyl-2-pyrrolidone → Isoxazole, 3-[3-bromo-2-methyl-6-(methylthio)phenyl]-4,5-dihydro-

HRID 1266572ノート

反応式

HRID 1266572 の反応式
[Br:1][C:2]1[C:3]([CH3:14])=[C:4]([C:9]2[CH2:13][CH2:12][O:11][N:10]=2)[C:5](Br)=[CH:6][CH:7]=1.CN1C(=O)CCC1.[CH3:22][S-:23].[Na+]>O>[Br:1][C:2]1[C:3]([CH3:14])=[C:4]([C:9]2[CH2:13][CH2:12][O:11][N:10]=2)[C:5]([S:23][CH3:22])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 13387N-methyl-2-pyrrolidoneHCID 4378561Sodium methanethiolateHCID 121004313-(3,6-Dibromo-2-methylphenyl)-4,5-dihydroisoxazole

生成物 1

HCID 9860657Isoxazole, 3-[3-bromo-2-methyl-6-(methylthio)phenyl]-4,5-dihydro-

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

25 g (0.075 mol) of 3-(3,6-dibromo-2-methylphenyl)-4,5-dihydroisoxazole are initially charged in 12 mol of NMP. At a temperature of 100° C. and at a reduced pressure of 100 mbar, 29.3 g (0.09 mol) of a 21.5% strength methanolic solution of sodium thiomethoxide are added dropwise over a period of 40 min. The reaction mixture is stirred at 100° C. for 3 h and then stirred into 250 ml of water and extracted three times with 100 ml of toluene. The combined organic phases are washed once with 100 ml of water and then concentrated under reduced pressure. This gives 17.5 g of a dark oil. GC/MS shows, in addition to other isomers, 52.3% of the desired product. MSm/z: 287.

後処理

  1. extractionextracted three times with 100 ml of toluene
  2. washThe combined organic phases are washed once with 100 ml of water
  3. concentrationconcentrated under reduced pressure
  4. additionGC/MS shows, in addition to other isomers, 52.3% of the desired product

出典と根拠

ORDレコード
ord-a7b617efce984e2382256668c9d4f530
出典データセット
uspto-grants-2003_04
特許番号
US06548677B1

反応ノート

読み込み中…