Hydrochloric Acid → HCID 12943046, compound

Participants

Reaction Conditions

Reaction Steps

4-(4-Nitrophenoxy)-3-methylphenyl methyl sulphide (120 g, 0.437 M) in 1.5 L of 95% ethanol was placed in a 3 L round bottom flask equipped with a stirrer, a reflux condenser, and a nitrogen inlet and a dropping funnel. After 6 ml of concentrated aqueous HCl had been added, 295 g of iron powder (excess, electrolytic iron, Matheson & Co.) was added over approximately 10 min in a slow stream at initial temperature 45° C. Stirring was continued for 1.5 hrs and then the reaction mixture was heated on steam under reflux and an additional 300 g of iron powder was added and stirring continued for 2 hr. more. The resulting suspension of iron and iron oxides was filtered with a filter aid [Supercel (Trade Mark)]. The clear filtrate and washes tended to darken in air moderately quickly. They were refiltered to remove the ferric hydroxide formed in contact with air, and immediately evaporated down on the steam bath at water pump pressure. The residue of this condensation was 82.2 g of a dark, rust-coloured liquid. This was dissolved in a total of 500 ml of water containing slightly over the theoretical amount of hydrochloric acid, and refiltered hot in the presence of more filter aid. The filter aid was washed with 200 ml more of hot water, and the whole aqueous filtrate was treated with concentrated hydrochloric acid until no more crystals appeared to come out, heated to near the boiling point, and cooled to approximately 40° C. The resulting white to salmon coloured solid was then filtered off. This melted at 162° C. and weighed 98 g. It was recrystallized from approximately 750 ml of hot water, adding a little aqueous hydrochloric acid to the washes and filtrates to retain the base in solution, then adding approximately 100 ml of concentrated hydrochloric acid and approximately 50 ml of water to the hot solution. It was cooled, and filtered at room temperature after about 1 hr. The product melted at 155°-158°, mostly at 157.5° C. Analysis: For C14H16ClNOS, M.W. 281.81: C, 59.66; H, 5.72; N, 4.97. Found: C, 59.52; H, 5.81; N, 4.82.

Provenance & Evidence