2-Methylaziridine → 2-Methyl-1-Tosyl-Aziridine

HRID 23775Notes

Reaction equation

HRID 23775 reaction equation
[CH3:1][CH:2]1[CH2:4][NH:3]1.[C:5]1([CH3:15])[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1>[OH-].[K+]>[CH3:1][CH:2]1[CH2:4][N:3]1[S:11]([C:8]1[CH:9]=[CH:10][C:5]([CH3:15])=[CH:6][CH:7]=1)(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 63772-MethylaziridineHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 5448752-Methyl-1-Tosyl-AziridineYield 58.5%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

2-Methylaziridine (3.6 ml, 51 mmol) was added to a 10% aqueous KOH solution (30 ml) and cooled in an ice bath for 30 min. To this solution p-toluenesulfonyl chloride (9.9 g, 52 mmol) was added rapidly while maintaining the temperature below 4° C. The resulting mixture was stirred for 30 min at 0° C., then stirred at room temperature overnight. The white precipitate was washed multiple times with cold water and dried under vacuum. The washed product was dissolved in hot petroleum ether and allowed to crystallize at 0° C., yielding colorless crystals (6.3 g, 57% yield).

Workup

  1. temperaturecooled in an ice bath for 30 min
  2. temperaturewhile maintaining the temperature below 4° C
  3. stirringstirred at room temperature overnight
  4. washThe white precipitate was washed multiple times with cold water
  5. customdried under vacuum
  6. dissolutionThe washed product was dissolved in hot petroleum ether
  7. customto crystallize at 0° C.

Sources & evidence

ORD record
ord-cf0ac7519533440aacba03633ef402c8
Source dataset
uspto-grants-2005_02
Patent number
US06852865B2

Reaction notes

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