Iodine → HCID 22567563, compound

Temperature

50 °C

Under an argon atmosphere, 70 ml of 1,4-dioxane were refluxed in a suitably equipped flask, 1 g of the product of step (b) was added, to give a clear solution after about 30 minutes, which was cooled to 50° C., followed by addition of 70 ml methanol, this flask being kept at 50° C. In a second flask, there was placed under an argon atmosphere, 1 g Mg turnings covered with methanol; two crystals of iodine were added, and after foaming began the mixture was stirred until the iodine color disappeared. The contents of the first flask were then poured into the second flask, and the temperature raised to 64° C. A further 1.4 g Mg turnings were added over 4 hours, and the reaction mixture was allowed to reflux for 5 days, until conversion as determined by UV was >95%. The mixture was cooled and poured into 500 ml of 20% NH4Cl solution extracted with 3×200 ml dichloromethane, washed with 5% aq. citric acid and water and rotoevaporated to give a solid which was dissolved in methanol and crystallized at −18° C. There were obtained 400 mg of the title compound as yellow crystals.

1. additionwas added
2. customto give a clear solution after about 30 minutes
3. custombeing kept at 50° C
4. customIn a second flask, there was placed under an argon atmosphere
5. additionThe contents of the first flask were then poured into the second flask
6. temperaturethe temperature raised to 64° C
7. temperatureto reflux for 5 days, until conversion
8. temperatureThe mixture was cooled
9. extractionextracted with 3×200 ml dichloromethane
10. washwashed with 5% aq. citric acid and water
11. customto give a solid which
12. customcrystallized at −18° C

ORD record

ord-6ad26364c6224d779e717a4a90e1f2ee

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07355054B2