Hydrochloric Acid → HCID 136348288, compound

Temperature

0 °C

In a 500 ml round bottom flask equipped with a magnetic stirrer was combined 26.0 g (126 mmol) 2-nitro-4-(trifluoromethyl)-aniline, 5.3 ml conc. HCl, 100 ml deionized water, and 150 ml ethanol. The mixture was cooled to 0° C. and sodium nitrite in 30 ml water was added dropwise over 60 minutes. The reaction mixture was stirred for an additional 1 hour and 300 mg sulfamic acid was added to destroy the excess nitrite. The solids were filtered and the cold filtrate was set aside. In a 1 liter flask was suspended (2-hydroxy-5-methoxy-1,3-phenylene)dimethanol in 200 ml deionized water and 100 ml ethanol. Approximately one-fourth of a solution of sodium hydroxide (25.4 g, 635 mmol) in 100 ml water was added to the phenolic mixture at 0° C. The diazonium salt mixture and remaining sodium hydroxide solution were added concurrently to the phenolic mixture over 1 hour. The reaction mixture was allowed to stir at 0° C. for 1 hour and room temperature for 4 hours. The mixture was poured in 3 liters water and the pH adjusted to 3-4 using 1N HCl. The solid was filtered and washed with ample amounts of water and then vacuum dried (0.1 mm Hg) at 55° C. for 40 hours to give 27.4 g (76%) of a red solid.

1. customIn a 500 ml round bottom flask equipped with a magnetic stirrer
2. customto destroy the excess nitrite
3. filtrationThe solids were filtered
4. customIn a 1 liter flask was suspended
5. additionwere added concurrently to the phenolic mixture over 1 hour
6. stirringto stir at 0° C. for 1 hour and room temperature for 4 hours
7. filtrationThe solid was filtered
8. washwashed with ample amounts of water
9. customvacuum dried (0.1 mm Hg) at 55° C. for 40 hours

ORD record

ord-3846720f6d0e4037be88ebc213f56a7e

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08232326B2