Methanol → Trinitrophloroglucinol

Picric acid (0.27 g, 1.20 mmol) and 4-amino-1,2,4-triazole (0.504 g, 6.00 mmol) are dissolved in a mixture of DMSO (3.6 ml) and toluene (4.8 ml) and treated with a 25 wt. % solution of sodium methoxide in methanol (3.00 ml, 13.1 mmol). The resulting suspension is stirred and heated from ambient temperature to 95° C. over a one hour period. The reaction suspension is cooled to ambient temperature prior to the addition of water (22.5 mL) and a 50% aqueous solution of sodium hydroxide (1.95 ml, 37.2 mmol). The brick-red suspension is stirred for 0.5 hour in a heated water bath (98–100° C.) and cooled in an ice bath for several hours. The resulting suspension is filtered and the resulting orange solid (trinitrophloroglucinol sodium salt) is collected and dissolved in hot 3N hydrochloric acid (16 ml). The resulting solution is cooled to ambient temperature prior to storage at 4° C. The crystalline product is collected, washed with cold 3N hydrochloric acid and dried to give trinitrophloroglucinol (0.211 g) in 67% overall yield.

1. temperatureheated from ambient temperature to 95° C. over a one hour period
2. stirringThe brick-red suspension is stirred for 0.5 hour in a heated water bath (98–100° C.)
3. temperaturecooled in an ice bath for several hours
4. filtrationThe resulting suspension is filtered
5. customthe resulting orange solid (trinitrophloroglucinol sodium salt) is collected
6. dissolutiondissolved in hot 3N hydrochloric acid (16 ml)
7. temperatureThe resulting solution is cooled to ambient temperature
8. customat 4° C
9. customThe crystalline product is collected
10. washwashed with cold 3N hydrochloric acid
11. customdried

ORD-Eintrag

ord-651c1fbf165e433babc3a694dc72729c

Quelldatensatz

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07057073B2