Dimethyl Sulfide → 1-(4-Methylbenzene-1-sulfonyl)-2,3-diphenylaziridine

HRID 1941478Notes

Reaction equation

HRID 1941478 reaction equation
CSC.[CH:4](=[N:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:22]1([CH:28]=[N+]=[N-])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>ClCCl.C(OC)(C)(C)C.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[C:5]1([CH:4]2[CH:28]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:11]2[S:12]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)(=[O:14])=[O:13])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 3

HCID 1068Dimethyl SulfideHCID 136601Benzene, (diazomethyl)-HCID 2755668N-tosyliMinobenzyliodinane

Product 1

HCID 27552431-(4-Methylbenzene-1-sulfonyl)-2,3-diphenylaziridine

Reagents, catalysts & solvents 3

HCID 21674Acetic acid, rhodium(2+) saltCatalystHCID 6344DichloromethaneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a stirred solution of dimethylsulphide (7 μl, 0.1 mmol), rhodium (II) acetate (2 mg, 0.005 mmol) and N-benzylidene-toluene-p-sulphonamide (131 mg, 0.5 mmol; J. C. S. Perkin I (1981) 2435-2442) in dichloromethane (2 ml) was added phenyldiazomethane (prepared as in Example 36; 8.11 ml of a 0.074M solution in t-butylmethylether) over a period of 12 hours. Upon completion of the addition, the solvent was removed in vacuo and the residue chromatographed using silica gel eluting with 15:85 ethyl acetate:petrol to give the title compound as a 3:1 mixture of trans:cis isomers (144 mg, 82%).

Workup

  1. customprepared as in Example 36
  2. additionUpon completion of the addition
  3. customthe solvent was removed in vacuo
  4. customthe residue chromatographed

Sources & evidence

ORD record
ord-a047363ee2b64b83b296bb0563ff4b99
Source dataset
uspto-grants-1997_12
Patent number
US05703246

Reaction notes

Loading…