Dichloromethane → 2-Chloro-[1,3]thiazolo[4,5-b]pyrazine

A mixture of 3H-thiazolo[4,5-b]pyrazine-2-thione (4.36 g, 25.8 mmol) and DCM (60 mL) was sonicated (5 min). The suspension was treated with sulfuryl chloride (99.9 g, 740 mmol, 60 mL) and heated (40° C., 16 h). The reaction mixture was cooled (0° C.) and slowly treated with H2O (250 mL), followed by 4 N NaOH (550 mL). The aqueous mixture was extracted with EtOAc (2×1800 mL). The organic layer was dried, filtered and concentrated in vacuo to provide the title compound as a solid (2.63 g, 53%). MS (ESI): mass calculated for C5H2ClN3S, 170.9; m/z found, 172.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 8.84 (d, J=2.5, 1H), 8.75 (d, J=2.5, 1H).

1. customwas sonicated (5 min)
2. temperatureThe reaction mixture was cooled (0° C.)
3. extractionThe aqueous mixture was extracted with EtOAc (2×1800 mL)
4. customThe organic layer was dried
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORDレコード

ord-2c3a96e95f924d329239787700849c73

出典データセット

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08399465B2