2-Bromopropane → 2-(Isopropylthio)aniline

To a solution of 2-aminothiophenol (90%, 100 g, 0.72 mol) and sodium hydroxide (31.7 g, 0.792 mol) in 90% aqueous ethanol (500 ml) was added dropwise 2-bromopropane (89 g, 0.72 mol) at room temperature. When the addition was complete, the reaction mixture was refluxed for 3 hours, cooled to room temperature, and then concentrated in vacuo. The residue was diluted with water (300 ml) and extracted with ether (3×500 ml). The ether extracts were washed with water and brine, dried with MgSO4 and concentrated in vacuo to yield the crude product. Distillation through a Vigreaux column gave 2-(1-methylethylthio)benzenamine: bp 94° (2.2-2.4 mm).

1. additionWhen the addition
2. temperaturethe reaction mixture was refluxed for 3 hours
3. concentrationconcentrated in vacuo
4. additionThe residue was diluted with water (300 ml)
5. extractionextracted with ether (3×500 ml)
6. washThe ether extracts were washed with water and brine
7. dry with materialdried with MgSO4
8. concentrationconcentrated in vacuo
9. customto yield the crude product
10. distillationDistillation through a Vigreaux column

ORD record

ord-305229975b5d41778d487869b6f2061c

Source dataset

uspto-grants-1989_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04818277