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

HRID 1868419Notes

Reaction equation

HRID 1868419 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-79aac52b5d7a482597ed54706951fe29
Source dataset
uspto-grants-2009_12
Patent number
US07635711B2

Reaction notes

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