Carbon Disulfide → HCID 12925584, compound

Temperature

0 °C

A solution of 2-methyl aniline (10.71 g, 100 mmol) in DMSO (50 mL) was treated with 20N aqueous NaOH (5 mL, 100 mmol) at room temperature. The mixture was cooled to 0° C. and CS2 (7.61 g, 100 mmol) was added. Upon stirring for 1 hour at room temperature, a change of color from dark-red to orange was observed. The solution was then cooled to 0° C. and chloroacetone (9.25 g, 100 mmol) was added. After stirring for 3 hours at room temperature, water (100 mL) was added and the mixture was stirred for an additional 10 minutes at 0° C. The precipitate was filtered and successively washed with water and ethanol. The crude product was suspended in 95% ethanol (100 mL), and 36% HCl (50 mL) was added and the mixture was heated to reflux for 1 hour. After cooling to room temperature, the precipitate was filtered to yield the desired product. (8.7 g, 38%)

1. temperatureThe solution was then cooled to 0° C.
2. stirringAfter stirring for 3 hours at room temperature
3. stirringthe mixture was stirred for an additional 10 minutes at 0° C
4. filtrationThe precipitate was filtered
5. washsuccessively washed with water and ethanol
6. addition36% HCl (50 mL) was added
7. temperaturethe mixture was heated
8. temperatureto reflux for 1 hour
9. temperatureAfter cooling to room temperature
10. filtrationthe precipitate was filtered

ORD record

ord-f0228256534e434ebd1f1b4286d3dfa3

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08748011B2