Hydrochloric Acid → HCID 86699690, compound

Temperature

60 °C

To a slurry of chloral hydrate (1.39 g, 8.4 mmol) and sodium sulfate (6.91 g, 48.7 mmol) in water (23.1 mL) was added benzo[d][1,3]dioxol-4-amine (1.0 g, 7.3 mmol), hydroxylamine sulfate (6.24 g, 38 mmol) and diluted hydrochloric acid (1.2 N, 7.7 mL). After stirring at 60° C. for 1.5 hours, the reaction mixture was kept at 25° C. overnight. The brown solid was collected by filtration and washed with water. After drying under vacuum, the solid was taken up in methane sulfonic acid and the solution was heated at 45° C. for 30 minutes. The mixture was cooled to 0° C. and then poured into ice (200 g). A dark red solid was precipitated and collected by filtration, dried to afford the product (635 mg, yield 53%). 1H NMR (400 MHz, CDCl3) δ ppm 7.68 (br s, 1H), 7.35-7.37 (d, 1H, J=8.0 Hz), 6.59-6.61 (d, 1H, J=8.0 Hz), 6.13 (s, 2H).

1. waitthe reaction mixture was kept at 25° C. overnight
2. filtrationThe brown solid was collected by filtration
3. washwashed with water
4. customAfter drying under vacuum
5. temperaturethe solution was heated at 45° C. for 30 minutes
6. temperatureThe mixture was cooled to 0° C.
7. additionpoured into ice (200 g)
8. customA dark red solid was precipitated
9. filtrationcollected by filtration
10. customdried

ORD record

ord-74c905959b494a4f9bb9b9b897a4468f

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428508B2