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

HRID 1868419

Reaktionsgleichung

Reaktionsgleichung von HRID 1868419
[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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 574740362-Trifluoromethyl-1-(2,4,6-trimethylbenzenesulfonyl)aziridineAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-79aac52b5d7a482597ed54706951fe29
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07635711B2

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