Benzene → Pyrazine, 2-methoxymethyl-5-methyl-, 4-oxide

2-Hydroxymethyl-5-methylpyrazine-4-oxide (3.5 g) was dissolved under stirring in a solution of 8 ml of thionyl chloride in 20 ml of dry benzene containing 0.5 g of ZnCl2, keeping the temperature below 30° C. The reaction mixture was cautiously warmed 3 hours at 60° C., then cooled to room temperature, and filtered. The solvent was evaporated under reduced pressure. The oily residue was dissolved in a solution of sodium methoxide in methyl alcohol, previously prepared dissolving 0.6 of sodium in 30 ml of methyl alcohol. After refluxing 4 hours, the reaction solution was cooled at room temperature, filtered and evaporated to dryness. The residue was taken up with water and repeatedly extracted with ethyl ether. The organic phase was washed with water, dried and the solvent was evaporated to dryness; the residue treated with pentane gave 2-methoxymethyl-5-methylpyrazine-4-oxide (1.5 g), m.p. 69°-72° C.

1. customthe temperature below 30° C
2. filtrationfiltered
3. customThe solvent was evaporated under reduced pressure
4. dissolutionThe oily residue was dissolved in a solution of sodium methoxide in methyl alcohol
5. custompreviously prepared
6. temperatureAfter refluxing 4 hours
7. temperaturethe reaction solution was cooled at room temperature
8. filtrationfiltered
9. customevaporated to dryness
10. extractionrepeatedly extracted with ethyl ether
11. washThe organic phase was washed with water
12. customdried
13. customthe solvent was evaporated to dryness
14. additionthe residue treated with pentane

ORDレコード

ord-15b32b1cc4314a388e091e2a013db558

出典データセット

uspto-grants-1983_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04406901