4-Toluenesulfonyl chloride → 2,2-Dimethyl-1-(toluene-4-sulfonyl)-aziridine

HRID 727959Notes

Reaction equation

HRID 727959 reaction equation
[CH3:1][C:2]1([CH3:5])[CH2:4][NH:3]1.[C:6]1([CH3:16])[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][CH:7]=1>N1C=CC=CC=1.CCOCC>[CH3:1][C:2]1([CH3:5])[CH2:4][N:3]1[S:12]([C:9]1[CH:10]=[CH:11][C:6]([CH3:16])=[CH:7][CH:8]=1)(=[O:14])=[O:13]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 2272442,2-Dimethylaziridine

Product 1

HCID 2783362,2-Dimethyl-1-(toluene-4-sulfonyl)-aziridineYield 26.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,2-dimethylaziridine (5.42 g; 0.076 mole; sold by Polysciences, Inc., Warrington, PA) in pyridine (100 mL) cooled in an ice bath, is added p-toluenesulfonyl chloride (21.81 g; 0.114 mole) in one portion. The reaction is stirred at 0° C. for 2 hours; diluted with ether (400 mL); washed with cold 10% H3PO4 (2×150 mL), with a saturated NaHCO3 solution (3×150 mL) and brine (1×150 mL); and dried over MgSO4. Rotary evaporation of the solution affords a yellowish solid which is crystallized from ethyl acetate to yield the product 2,2-dimethyl-N-p-toluenesulfonyl-aziridine (4.48 g). 1H NMR (CDCl3):1.53 (6H, s), 2.45 (5H, m), 7.2-8.0 ppm (4H, m, aromatics).

Workup

  1. washwashed with cold 10% H3PO4 (2×150 mL), with a saturated NaHCO3 solution (3×150 mL) and brine (1×150 mL)
  2. dry with materialand dried over MgSO4
  3. customRotary evaporation of the solution
  4. customaffords a yellowish solid which
  5. customis crystallized from ethyl acetate

Sources & evidence

ORD record
ord-b255ca49770e4284875eec9536d61e99
Source dataset
uspto-grants-1991_09
Patent number
US05045565

Reaction notes

Loading…