Ethanol → HCID 608034, compound

A reaction mixture was prepared containing 68.7 g. of 3-methylthio-4-nitroveratrole, 261 g. sodium dithionite (Na2S2O4), 1500 ml. of ethanol and 2250 ml. of water. The reaction mixture was heated at reflux temperature for about 1 hour and then cooled. The reaction mixture was then made basic with potassium carbonate and the resulting alkaline solution concentrated in vacuo to one-half its original volume. The aqueous solution was extracted twice with 2 l. portions of ether. The ether extracts were combined, dried, and the ether removed therefrom by evaporation in vacuo. The solid residue, comprising 2-methylthio-4,5-dimethoxy aniline formed in the above reaction, was recrystallized from a benzene-hexane solvent mixture to yield 33.6 g. of crystalline material melting at 69°-72° C.

1. customA reaction mixture was prepared
2. additioncontaining 68.7 g
3. temperatureThe reaction mixture was heated
4. temperatureat reflux temperature for about 1 hour
5. temperaturecooled
6. concentrationthe resulting alkaline solution concentrated in vacuo to one-half its original volume
7. extractionThe aqueous solution was extracted twice with 2 l
8. customdried
9. customthe ether removed
10. customby evaporation in vacuo
11. customformed in the above reaction
12. customwas recrystallized from a benzene-hexane solvent mixture
13. customto yield 33.6 g

ORD record

ord-7e1b81fbac03489eaba50e6bed984de6

Source dataset

uspto-grants-1979_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04171361