反应详情

温度

210 °C

Put di(2-tolyl)amine (11.7 g, 59.3 mmol) in a 3-neck 100 mL round-bottom flask and added elemental sulfur (3.9 g, 121.65 mmoles, 2 eq.), crushed iodine (0.44 g, 1.73 mmoles, 3 mole %), then o-dichlorobenzene (22 mL). Added an outlet to a dilute bleach solution (for hydrogen sulfide evolution) then put under argon. Refluxed at 180° C. for 4 h. Removed solvent under reduced pressure. Purified with column chromatography using 2% ethyl acetate/98% hexane to obtain product as white crystals (2 g, 8.8 mmoles, 15% yield). (Alternatively, put di(2-tolyl)amine (either purified or impure from the aforementioned reaction; 8.9525 g, 45.3 mmoles) in a round bottom flask. Added elemental sulfur (2.98 g, 92.9 mmoles, 2 eq.) then crushed iodine (3.28 g, 12.9 mmoles, 28% mole). Added an outlet to a dilute bleach solution (for hydrogen sulfide) then put under argon. Stirred at 210° C. for 30 min or until no starting material was present by LC/MS. Let the reaction cool to about 60° C. then added hexane for extraction. Repeated hot hexane extractions (at least one overnight; minimum time of half an hour for each extraction) of reaction until product was no longer seen in residue (about 4 times). Combined hexane extractions and concentrate in vacuo. Purified resulting residue either through repeated hot acetone/isopropanol crystallizations (or triturations) or Isco column chromatography using 2% ethyl acetate/98% hexane to obtain product as white crystals (2.92 g, 12.8 mmoles, 28% yield).)

1. custompurified
2. customimpure from the aforementioned reaction
3. temperaturecool to about 60° C.
4. extractionadded hexane for extraction
5. extractionhexane extractions (at least one overnight
6. extractionminimum time of half an hour for each extraction)
7. customof reaction until product
8. extractionCombined hexane extractions
9. concentrationconcentrate in vacuo
10. customPurified
11. customresulting residue
12. customacetone/isopropanol crystallizations (or triturations) or Isco column chromatography