Hydrochloric Acid → HCID 25152599, Verbindung

A solution of 3-amino-5-methylthiophene-2-carbonitrile (250 mg, 1.0 eq., 1.81 mmol) and sulfamoyl chloride (2.71 mmol, 1.5 eq., 314 mg) in DMA (5 mL) was stirred at room temperature overnight. Water (30 mL) and NaOH (1.5 eq., 10 N, 2.71 mmol, 271 μL) were added and the mixture was frozen in a dry ice/acetone bath and the volatiles were removed on the lyophilizer. The resulting solid was washed with water and then suspended in EtOH (25 mL, 200 proof). To this suspension was added NaOH (1 N, 2.5 eq., 4.52 mmol, 4.52 mL) and the mixture heated to reflux for 45 minutes. The reaction mixture was cooled to room temperature and quenched with HCl (1 N, 2.5 eq., 4.52 mmol, 4.52 mL). The pH was adjusted to ˜1-2 with 1 N HCl and the volatiles removed on a rotary evaporator. The resulting solid was suspended in water (10 mL), stirred, filtered off, and washed with water. The crude product was dried in a vacuum oven to give 6-methyl-1H-thieno[3,2-c][1,2,6]thiadiazin-4-amine-2,2-dioxide (257 mg) as an off-white powder 1H NMR (400 MHz, DMSO-d6) δ 2.46 (d, J=0.8 Hz, 3H), 6.53 (q, J=0.8 Hz, 1H), 7.75 (br. s, 2H), 11.34 (s, 1H). 1H NMR (400 MHz, CD3OD) δ 2.52 (d, J=0.8 Hz, 3H), 6.55 (q, J=0.8 Hz, 1H). MS 218 (MH+).

1. temperaturethe mixture was frozen in a dry ice/acetone bath
2. customthe volatiles were removed on the lyophilizer
3. washThe resulting solid was washed with water
4. temperaturethe mixture heated
5. temperatureto reflux for 45 minutes
6. customthe volatiles removed on a rotary evaporator
7. filtrationfiltered off
8. washwashed with water
9. dry with materialThe crude product was dried in a vacuum oven

ORD-Eintrag

ord-9cf0cfa52c904fd6acef9b3cca3fa853

Quelldatensatz

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09181276B2