Iodine → HCID 90418750, compound

Temperature

-78 °C

Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed tetrahydrofuran (15 mL). This was followed by the addition of bis(propan-2-yl)amine (1.34 g, 13.24 mmol, 1.50 equiv). The mixture was cooled to −78° C. To this was added n-BuLi (2.5M) (5.28 mL). The mixture was stirred at −78° C. for 40 minutes. To the mixture was added a solution of ethyl 3-(4-ethylphenyl)-1,2-thiazole-4-carboxylate (2.3 g, 8.80 mmol, 1.00 equiv) in tetrahydrofuran (5 mL). The mixture was stirred at −78° C. for 40 minutes. To the mixture was added a solution of I2 (3.35 g, 13.19 mmol, 1.50 equiv) in tetrahydrofuran (5 mL). The resulting solution was stirred for 40 min at −78° C. The reaction was then quenched by the addition of 80 mL of water. The resulting solution was extracted with 3×80 mL of ethyl acetate and the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:20). The collected fractions were combined and concentrated under vacuum. This resulted in 2.1 g (62%) of ethyl 3-(4-ethylphenyl)-5-iodo-1,2-thiazole-4-carboxylate as red oil.

1. customInto a 100-mL round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. stirringThe mixture was stirred at −78° C. for 40 minutes
4. stirringThe resulting solution was stirred for 40 min at −78° C
5. customThe reaction was then quenched by the addition of 80 mL of water
6. extractionThe resulting solution was extracted with 3×80 mL of ethyl acetate
7. concentrationconcentrated under vacuum
8. washeluted with ethyl acetate/petroleum ether (1:20)
9. concentrationconcentrated under vacuum
10. customThis resulted in 2.1 g (62%) of ethyl 3-(4-ethylphenyl)-5-iodo-1,2-thiazole-4-carboxylate as red oil

ORD record

ord-4d085a45bad04b148e2720bf6cd5ed2c

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1