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Ethylene → 3-(3-Bromo-2-methyl-6-(methylsulfonyl)phenyl)-4,5-dihydroisoxazole

HRID 49686
ノート
印刷プレビュー

反応式

HRID 49686 の反応式
ClN1C(=O)C[CH2:4][C:3]1=O.[Br:9][C:10]1[C:11]([CH3:23])=[C:12]([C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:17][CH:18]=1)[CH:13]=[N:14][OH:15].C=C.C(N(CC)CC)C>CN(C)C=O>[Br:9][C:10]1[C:11]([CH3:23])=[C:12]([C:13]2[CH2:4][CH2:3][O:15][N:14]=2)[C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:17][CH:18]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6325Ethylene2 回HCID 8471TriethylamineHCID 31398Chlorosuccinimide2 回HCID 734619443-Bromo-2-methyl-6-methylsulfonylbenzaldoxime

生成物 1

HCID 109470753-(3-Bromo-2-methyl-6-(methylsulfonyl)phenyl)-4,5-dihydroisoxazole

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

At 60° C., a small amount of N-chlorosuccinimide is added to a solution of 50 g (171 mmol) of 3-bromo-2-methyl-6-methylsulfonylbenzaldoxime in 200 ml of dimethylformamide. Once the reaction has started, a total of 23.3 g (171 mmol) of N-chlorosuccinimide are metered in at 40-50° C. The reaction mixture is stirred for another 30 minutes, until conversion is complete according to HPLC. The reaction mixture is then poured onto ice-water and the solid is filtered off with suction, washed three times with water and twice with n-pentane. The hydroxamic acid chloride is used moist and without further purification for the next reaction. The solid is dissolved in 250 ml of dichloromethane, and ethylene is passed through the solution. With continued introduction of ethylene, 20.3 q (200 mmol) of triethylamine are added dropwise. The reaction mixture is stirred at room temperature for about 72 hours, with repeated introduction of more gaseous ethylene.

後処理

  1. customare metered in at 40-50° C
  2. additionThe reaction mixture is then poured onto ice-water
  3. filtrationthe solid is filtered off with suction
  4. washwashed three times with water
  5. customThe hydroxamic acid chloride is used moist and without further purification for the next reaction
  6. dissolutionThe solid is dissolved in 250 ml of dichloromethane
  7. additionare added dropwise
  8. stirringThe reaction mixture is stirred at room temperature for about 72 hours

出典と根拠

ORDレコード
ord-db6485699bc747fab99ba9da3a1d8b72
出典データセット
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06706886B2

反応ノート

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