P-Toluenesulfonamide → Trans-2-(4-Methoxyphenyl)-3-phenyl-1-(4-methylphenylsulphonyl)aziridine

HRID 1941480Notes

Reaction equation

HRID 1941480 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17]([NH2:20])(=[O:19])=[O:18])=[CH:13][CH:12]=1.B(F)(F)F>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([C@H:7]2[C@H:7]([C:6]3[CH:9]=[CH:10][CH:3]=[CH:4][CH:5]=3)[N:20]2[S:17]([C:14]2[CH:13]=[CH:12][C:11]([CH3:21])=[CH:16][CH:15]=2)(=[O:18])=[O:19])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6269P-ToluenesulfonamideHCID 6356Boron trifluorideHCID 312444-Methoxybenzaldehyde

Product 1

HCID 12012745Trans-2-(4-Methoxyphenyl)-3-phenyl-1-(4-methylphenylsulphonyl)aziridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Methoxybenzaldehyde (1.22 ml, 10 mmol) and p-toluenesulphonamide (1.71 g, 10 mmol) were refluxed in toluene (70 ml) for 5 minutes using a Dean and Stark apparatus. Reflux was maintained while BF3 (C2 H5)2O (0.05 ml, 0.4 mmol) was added via a syringe. The reaction mixture was maintained at reflux for 12 hours before being allowed to cool to room temperature whereby the title compound precipitated from the toluene. Filtration followed by recrystallisation from dichloromethane-petrol yielded N-(4-methoxybenzylidene)-toluene-p-sulphonamide as a yellow solid (0.478 g; 17%) m.p. 127° C.

Workup

  1. temperatureReflux
  2. additionwas added via a syringe
  3. temperatureThe reaction mixture was maintained
  4. temperatureat reflux for 12 hours

Sources & evidence

ORD record
ord-ac39e9d4939f450584a8425b12564328
Source dataset
uspto-grants-1997_12
Patent number
US05703246

Reaction notes

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