2-Aminothiophenol → HCID 4575136, compound

To a solution of 2-aminothiophenol (93%, 123 g, 0.910 mol) and sodium hydroxide (40.2 g, 1.00 mol) in 90% aqueous ethanol (637 ml) was added dropwise 2-bromoethylmethylether (127 g, 0.910 mol) at room temperature. When the addition was complete, the reaction mixture was refluxed for 2 hours, cooled to room temperature, and then concentrated in vacuo. The resulting residue was diluted with water (1400 ml) and extracted with methylene chloride (3×500 ml). The extracts were washed with water (2×500 ml) and brine (500 ml), dried with (MgSO4), filtered and concentrated to give a dark oil. Distillation of the crude product gave 2-(2-methoxyethylthio)benzenamine (148 g, 89%) as a light yellow oil; bp 90°-103° (0.1 mm).

1. additionWhen the addition
2. temperaturethe reaction mixture was refluxed for 2 hours
3. concentrationconcentrated in vacuo
4. additionThe resulting residue was diluted with water (1400 ml)
5. extractionextracted with methylene chloride (3×500 ml)
6. washThe extracts were washed with water (2×500 ml) and brine (500 ml)
7. dry with materialdried with (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customto give a dark oil
11. distillationDistillation of the crude product

ORD record

ord-c57de50505eb4c19b657273785d5b9bd

Source dataset

uspto-grants-1985_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04528024