Hydrochloric Acid → HCID 13882880, compound

Participants

Reaction Steps

A mixture of 5.0 g (0.016 mol) of product of Example 5, 8.38 g (0.154 mol) of KOH, 45 ml of water in 100 ml of ethanol were refluxed for 16 hours. The reaction mixture was poured into 250 ml of water containing 50 ml of HCl, extracted with ether, dried (MgSO4) and concentrated in vacuo to 3.35 g of solid. Then 45 ml of SOCl2 was added to the solid and this was refluxed for 2 hours. Reaction mixture was concentrated in vacuo and 45 ml of methanol was added to the residue and refluxed for 16 hours. Reaction mixture was concentrated in vacuo. The residue was dissolved in ether, extracted with 10% K2CO3, and water. The combined aqueous layers were acidified with concentrated HCl, extracted with ether, dried (MgSO4) and concentrated in vacuo to 2.11 g of white solid. To this solid was added 1.21 ml (0.010 mol) of 2,6 -lutidine and 20 ml of POCl3. This was refluxed for 16 hours. The reaction mixture was concentrated in vacuo. The residue was poured into water, extracted with ether, washed with 10% HCl, dried (MgSO4) and concentrated in vacuo to 2.17 g of brown oil. Then 50 ml of MeOH was added and this was refluxed for 31/2 hours and then stirred at room temperature for 72 hours. The reaction mixture was concentrated in vacuo to 1.88 g of crude produt. Kugelrohr distillaton at 47 Pa, pot temperature 80° C., afforded 1.55 g (68.3%) of product as a clear oil, nD25 1.4493.

Provenance & Evidence