1-[(Methylsulfanyl)methyl]-2-nitrobenzene → 2-[(Methylsulfanyl)methyl]aniline

Iron powder (60 g, 1.0 g-atom) was added slowly through a solid addition funnel to a solution of 53.5 g (0.29 mol) of o-methylthiomethylnitrobenzene in 210 ml of glacial acetic acid and 600 ml of absolute ethanol under reflux over a period of 45 minutes. The mixture was then refluxed for 3 hours. The iron powder was filtered off and the filtrate was diluted with 800 ml of water. The aqueous mixture was extracted twice with 200 ml ethyl acetate and twice with 200 ml ether. The combined organic extracts were washed with water, dried and concentrated to yield 48 g (75% pure) of orange oil.

1. temperatureunder reflux over a period of 45 minutes
2. temperatureThe mixture was then refluxed for 3 hours
3. filtrationThe iron powder was filtered off
4. additionthe filtrate was diluted with 800 ml of water
5. extractionThe aqueous mixture was extracted twice with 200 ml ethyl acetate and twice with 200 ml ether
6. washThe combined organic extracts were washed with water
7. customdried
8. concentrationconcentrated
9. customto yield 48 g (75% pure) of orange oil

ORD record

ord-0e33b23b59f745929dd52f3c0a765561

Source dataset

uspto-grants-1982_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04348220