Sodium Carbonate → 6-(Dimethylamino)hexane-1-thiol

Participants

Reaction Steps

6-dimethylaminohexanol was suspended in CH2Cl2 and treated with p-toluenesulphonic anhydride in the presence of triethylamine for 1 hour at 0° C. The reaction mixture was then treated with potassium thioacetate in DMF at 50° C. for a further hour. The resulting compound, AcS(CH2)6NMe2, was treated with sodium carbonate in methanol at room temperature for 20 hours to give 6-(dimethylamino)hexanethiol. This was suspended in dry DMSO at room temperature and sodium hydride was added. The reaction mixture was left stirring for 30 mixtures. 5-bromo-2-thiophenecarboxaldehyde in DMSO was then added and the reaction mixture was warmed to 80° C. for 30 minutes to give the title compound. This is the starting aldehyde used in the preparation of compound 5442.

Provenance & Evidence