Methyl iodide → HCID 13341919, compound

A suspension of 3,4-dihydro-6-hydroxy-2-trichloromethyl-2H-benzo[e]-[1,3]-oxazin-4-one (prepared as described in Example 3--2.5 g.) in ethanol (125 ml.) was stirred, ethanolic sodium hydroxide (32 ml. of a 0.36 M solution) was added, and the mixture was stirred for 30 minutes. Iodomethane (1.5 ml.) was added, and the solution was heated on a steam-bath for 1 hour. The solvent was evaporated under reduced pressure, and the residue was dissolved in a mixture of diethyl ether (100 ml.) and N sodium hydroxide solution (50 ml.). The ether layer was separated, the aqueous layer was re-extracted with ether (100 ml.), and the ether extracts were combined and dried. The solvent was evaporated, and the sticky residue was stirred for 15 minutes with petroleum ether (b.p. 60°-80°, 100 ml.). then filtered and washed with more petroleum ether to yield 3,4-dihydro-6-methoxy-2-trichloromethyl-2H-benzo[e]-[1,3]-oxazin-4-one, m.p. 162°-165° C.

1. stirringthe mixture was stirred for 30 minutes
2. temperaturethe solution was heated on a steam-bath for 1 hour
3. customThe solvent was evaporated under reduced pressure
4. dissolutionthe residue was dissolved in a mixture of diethyl ether (100 ml.) and N sodium hydroxide solution (50 ml.)
5. customThe ether layer was separated
6. extractionthe aqueous layer was re-extracted with ether (100 ml.)
7. customdried
8. customThe solvent was evaporated
9. stirringthe sticky residue was stirred for 15 minutes with petroleum ether (b.p. 60°-80°, 100 ml.)
10. filtrationthen filtered
11. washwashed with more petroleum ether

ORD record

ord-77baf844328d4c8497b5e9f6aa492db6

Source dataset

uspto-grants-1981_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04268510