Acetone Cyanohydrin → HCID 178463114、化合物

HRID 1857320

反応式

HRID 1857320 の反応式
Cl.[CH2:2]([N:4]1[C:8]([OH:9])=[CH:7][CH:6]=[N:5]1)[CH3:3].C(N(CC)CC)C.[O:17]1[CH2:21][CH2:20][C:19]([C:22]2[C:23]([CH3:35])=[C:24]([CH:28]=[CH:29][C:30]=2[S:31]([CH3:34])(=[O:33])=[O:32])[C:25](Cl)=[O:26])=[N:18]1.CC(C)(O)C#N>C(Cl)(Cl)Cl>[O:17]1[CH2:21][CH2:20][C:19]([C:22]2[C:23]([CH3:35])=[C:24]([CH:28]=[CH:29][C:30]=2[S:31]([CH3:34])(=[O:33])=[O:32])[C:25]([C:7]2[CH:6]=[N:5][N:4]([CH2:2][CH3:3])[C:8]=2[OH:9])=[O:26])=[N:18]1

参加物

6

反応物 4

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2 回HCID 112550833-(4,5-Dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoyl chlorideHCID 178463041HCID 178463041、化合物

生成物 1

HCID 178463114HCID 178463114、化合物収率 67.3%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

To 2.75 g of 3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoic acid were added 30 ml of benzene, then 1.7 ml of thionyl chloride and a drop of pyridine to heat at reflux for 3 hours. The reaction solution was cooled down. The solvent was distilled out under reduced pressure to give 2.90 g of 3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoyl chloride. Separately 0.93 g of 1-ethyl-5-hydroxypyrazole hydrochloride was dissolved in 20 ml of chloroform, and 1.60 g of triethylamine was added, while cooling with ice. Into the obtained solution was added dropwise 10 ml of a chloroform solution containing 1.90 g of 3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoyl chloride to stir at room temperature for 30 minutes, and 0.76 g of triethylamine and 0.16 g of acetone cyanohydrin were added to further stir overnight. The reaction solution was washed with dilute hydrochloric acid, then with a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was distilled out under reduced pressure. Methanol was added to the residue. The obtained crystals were separated by filtration to give 1.59 g of the title compound as white crystals. m.p. 183~184.5° C.

後処理

  1. temperaturewhile cooling with ice
  2. washThe reaction solution was washed with dilute hydrochloric acid
  3. dry with materialwith a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled out under reduced pressure
  5. additionMethanol was added to the residue
  6. customThe obtained crystals were separated by filtration

出典と根拠

ORDレコード
ord-5dfc44ea4ec545fa92afe03413a59bb1
出典データセット
uspto-grants-2000_11
特許番号
US06147031

関連ノート

読み込み中…