4-Toluenesulfonyl chloride → 2-Trifluoromethyl-1-(2,4,6-trimethylbenzenesulfonyl)aziridine

HRID 1868419

反応式

HRID 1868419 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10]([NH:13][CH:14]([CH2:19]O)[C:15]([F:18])([F:17])[F:16])(=[O:12])=[O:11].[H-].[Na+].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C1COCC1.O>[F:16][C:15]([F:18])([F:17])[CH:14]1[CH2:19][N:13]1[S:10]([C:3]1[C:2]([CH3:1])=[CH:7][C:6]([CH3:8])=[CH:5][C:4]=1[CH3:9])(=[O:12])=[O:11]

参加物

6

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 574740352,4,6-trimethyl-N-(2,2,2-trifluoro-1-hydroxymethylethyl)benzenesulfonamide

生成物 1

HCID 574740362-Trifluoromethyl-1-(2,4,6-trimethylbenzenesulfonyl)aziridine収率 99.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 690 mg (2.22 mmol) of 2,4,6-trimethyl-N-(2,2,2-trifluoro-1-hydroxymethylethyl)benzenesulfonamide in 10 mL of THF was added 180 mg (4.5 mmol) of 60% sodium hydride in mineral oil in several portions followed by 475 mg (2.5 mmol) of p-toluenesulfonyl chloride. The mixture stirred at room temperature over night and was then diluted with water and extracted with three 20 mL portions of ethyl acetate. The combined organic layers were washed with three 20 mL portions of saturated aqueous sodium bicarbonate solution, 20 mL of brine, and two 20 mL portions of saturated aqueous ammonium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 650 mg (99%) of 2-trifluoromethyl-1-(2,4,6-trimethylbenzenesulfonyl)aziridine as an oil which solidified to a waxy solid upon standing.

後処理

  1. extractionextracted with three 20 mL portions of ethyl acetate
  2. washThe combined organic layers were washed with three 20 mL portions of saturated aqueous sodium bicarbonate solution, 20 mL of brine, and two 20 mL portions of saturated aqueous ammonium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-79aac52b5d7a482597ed54706951fe29
出典データセット
uspto-grants-2009_12
特許番号
US07635711B2

関連ノート

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