Methyl iodide → HCID 10219842, compound

Temperature

6 °C

Dimethyl phosphite (11.0 g 0.1 mol) was added dropwise to a stirred solution of 2.4 g (0.1 mole) of sodium hydride in 50 mL of dry THF at 25-30° C. under N2. The mixture was stirred under reflux until H2 evolution ceased. It was then cooled to 6° C. and was added with stirring to carbon disulfide (38 g, 0.5 mol) at 2-8° C. over 15 min. Methyl iodide (14.2 g 0.1 mol) was then added at 5° C. over 15 min. The mixture was quenched with 350 mL of ice-water and extracted with ether (100 mL×3). The ether layers were combined, dried with anhydrous magnesium sulfate, filtered, evaporated to remove ether and distilled in vacuo. The fraction boiling between 92-94° C./50μ was collected, 6.5 g, Y=32.5%. (Put footnote 2 here) 1H NMR: δ (ppm) 3.85 (d, 6H, 3JHP=10 Hz, POCH3), 2.69 (d, 3H, JHP=1 Hz CSCH3); 13C NMR: δ (ppm) 228(d, 1JCP=175 Hz, CS), 54.5 (d, 2J CP=6 Hz, POCH3), 10.9 (s, CSCH3); 31P NMR {H}: δ (ppm) 0.30 (s); 31P NMR: δ (ppm) 0.30 (m, 3JPH=11 Hz); HRMS: 199.9732 (Found); 199.9731 (Calcd).

1. temperatureunder reflux until H2 evolution
2. additionwas added
3. customThe mixture was quenched with 350 mL of ice-water
4. extractionextracted with ether (100 mL×3)
5. dry with materialdried with anhydrous magnesium sulfate
6. filtrationfiltered
7. customevaporated
8. customto remove ether
9. distillationdistilled in vacuo
10. customboiling between 92-94° C.
11. customwas collected

ORD record

ord-b0344003d99c4f268821a620598c3414

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06441214B1