Hydrochloric Acid → 4-Bromo-2-(4,5-dihydroisoxazol-3-yl)-3-methylbenzenesulfonyl chloride

HRID 49672

反応式

HRID 49672 の反応式
[Br:1][C:2]1[CH:8]=[CH:7][C:5](N)=[C:4]([C:9]2[CH2:13][CH2:12][O:11][N:10]=2)[C:3]=1[CH3:14].[ClH:15].N([O-])=O.[Na+].[S:20](=[O:22])=[O:21]>C(O)(=O)C.O.[Cu](Cl)Cl>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([S:20]([Cl:15])(=[O:22])=[O:21])=[C:4]([C:9]2[CH2:13][CH2:12][O:11][N:10]=2)[C:3]=1[CH3:14]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 9813747Benzenamine, 4-bromo-2-(4,5-dihydro-3-isoxazolyl)-3-methyl-HCID 23668193Sodium Nitrite

生成物 1

HCID 187572534-Bromo-2-(4,5-dihydroisoxazol-3-yl)-3-methylbenzenesulfonyl chloride

試薬・触媒・溶媒 3

HCID 24014Cupric Chloride触媒HCID 176Acetic Acid溶媒2 回HCID 962Water溶媒2 回

反応条件

温度
5 °C

実験手順

At 15° C., a solution of 9 g (35 mmol) of 4-bromo-2-(4,5-dihydroisoxazol-3-yl)-3-methylaniline in 50 ml of glacial acetic acid is added to 15 ml of conc. hydrochloric acid. At 5-10° C., a solution of 2.44 g (35 mmol) of sodium nitrite in 10 ml of water is then added dropwise, and the mixture is stirred at 5° C. for 1 hour. At room temperature, this solution is then added dropwise to a mixture of a solution of 47 g (0.74 mol) of sulfur dioxide in 100 ml of glacial acetic acid and a solution of 2.23 g (13 mmol) of copper(II) chloride in 5 ml of water. The reaction mixture is stirred at room temperature for 1 hour and subsequently poured into 300 ml of ice-water and extracted with methylene chloride. The organic phase is washed with water, dried with magnesium sulfate and concentrated.

後処理

  1. stirringThe reaction mixture is stirred at room temperature for 1 hour
  2. extractionextracted with methylene chloride
  3. washThe organic phase is washed with water
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-ca4ace3ab43043a2a08b5f0069a97f16
出典データセット
uspto-grants-2004_03
特許番号
US06706886B2

関連ノート

読み込み中…