HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Dimethyl Sulfide → Trans-2-(4-Methoxyphenyl)-3-phenyl-1-(4-methylphenylsulphonyl)aziridine
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Dimethyl Sulfide | HCID 1068 | — |
| Edukt | Benzene, (diazomethyl)- | HCID 136601 | — |
| Edukt | N-[(4-Methoxyphenyl)methylidene]-4-methylbenzene-1-sulfonamide | HCID 766935 | — |
| Katalysator | Acetic acid, rhodium(2+) salt | HCID 21674 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Lösungsmittel | tert-Butyl methyl ether | HCID 15413 | — |
| Produkt | Trans-2-(4-Methoxyphenyl)-3-phenyl-1-(4-methylphenylsulphonyl)aziridine | HCID 12012745 | 51% |
Reaktionsschritte
To a stirred solution of dimethylsulphide (7 μl, 0.1 mmol), rhodium (II) acetate (2 mg, 0.005 mmol) and N-(4-methoxybenzylidene)toluene-p-sulphonamide (144 mg, 0.5 mmol) in dichloromethane (2 ml) was added phenyldiazomethane (prepared as in Example 36; 8.96 ml of a 0.067M solution in t-butylmethylether) over a period of 12 hours. Upon completion of the addition the solvent was removed in vacuo and the residue was chromatographed using silica gel eluting with 15:85 ethyl acetate:petrol to give the title compound (96 mg, 51%). δH (CDCl3) 7.62(2H), 6.75-7.45(11H,m), 4.35(1H,d,J=6 Hz), 4.18(1H,d,J=6 Hz), 3.62(3H,s), 2.35(3H,s)ppm.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US05703246 |
| Quelldatensatz | uspto-grants-1997_12 |
| ORD ID | ord-fff2ba1b05d24dbb91544fb1260fe7d5 |
| Quellennotiz | uspto-grants-1997_12 |