Hydrochloric Acid → HCID 12943046, compound

Temperature

40 °C

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.

1. customequipped with a stirrer, a reflux condenser, and a nitrogen inlet and a dropping funnel
2. temperaturethe reaction mixture was heated on steam
3. temperatureunder reflux
4. stirringstirring
5. waitcontinued for 2 hr
6. filtrationwas filtered with a filter aid [Supercel (Trade Mark)]
7. customto remove the ferric hydroxide
8. customformed in contact with air
9. customimmediately evaporated down on the steam bath at water pump pressure
10. dissolutionThis was dissolved in a total of 500 ml of water containing slightly over the theoretical amount of hydrochloric acid
11. filtrationof more filter aid
12. washThe filter aid was washed with 200 ml more of hot water
13. additionthe whole aqueous filtrate was treated with concentrated hydrochloric acid until no more crystals
14. temperatureheated to near the boiling point
15. filtrationwas then filtered off
16. customIt was recrystallized from approximately 750 ml of hot water
17. additionadding a little aqueous hydrochloric acid to the washes and filtrates
18. additionadding approximately 100 ml of concentrated hydrochloric acid and approximately 50 ml of water to the hot solution
19. temperatureIt was cooled
20. filtrationfiltered at room temperature after about 1 hr
21. custommostly at 157.5° C

ORD record

ord-d405998cf0f740a39b8fde8783629699

Source dataset

uspto-grants-1982_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04329365