Dimethyl Sulfoxide → HCID 66604971, compound

Temperature

80 °C

A 1 L, 4 neck RBF was equipped with a thermowell, condenser with a nitrogen inlet, stopper and mechanical stirrer. The RBF was charged with chloroethylnorbornene (100 g, 0.64 mol), 300 mL DMSO and solid NaCN (43.8 g, 0.89 mol). An extra 20 mL DMSO was added to rinse in the NaCN. The reaction mixture was stirred at ˜80° C. for 2 hours. GC analysis of an aliquot indicated all starting material had been consumed and the reaction was completed. The reaction mixture was cooled to room temperature. Approximately 200 mL water was poured into the flask and diluted with 100 mL MTBE. The organic phase was separated and the aqueous layer was re-extracted with (3×200 mL) MTBE. The organic phases were combined and washed with (3×500 mL) tap water until the aqueous wash reached pH=6. The MTBE solution was dried over anhydrous sodium sulfate overnight, filtered, and rotary evaporated to give 93.5 g (99.5% yield) with 99.3% purity by GC. NMR analysis indicated the material contained ˜1% MTBE. The crude product was used for the next reaction without further purification. Data: GC analysis done on a DB5 Column, 30 meters, 0.32 mm ID, 0.25 μm film, 75° C. to 300° C. at 25° C./min., hold for 2 min at 300° C., Injector temperature: 275° C., Detector temperature: 350° C.

1. customA 1 L, 4 neck RBF was equipped with a thermowell, condenser with a nitrogen inlet
2. washto rinse in the NaCN
3. customhad been consumed
4. temperatureThe reaction mixture was cooled to room temperature
5. additionApproximately 200 mL water was poured into the flask
6. additiondiluted with 100 mL MTBE
7. customThe organic phase was separated
8. extractionthe aqueous layer was re-extracted with (3×200 mL) MTBE
9. washwashed with (3×500 mL)
10. washaqueous wash
11. dry with materialThe MTBE solution was dried over anhydrous sodium sulfate overnight
12. filtrationfiltered
13. customrotary evaporated
14. customto give 93.5 g (99.5% yield) with 99.3% purity by GC
15. customdone on a DB5 Column, 30 meters, 0.32 mm ID, 0.25 μm film, 75° C. to 300° C. at 25° C./min.
16. waithold for 2 min at 300° C.
17. custom275° C., Detector temperature
18. custom350° C.

ORD record

ord-ab922b2df82c46599f31298971df4da1

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09175123B2