Trifluoroacetic acid → 4-Ethylsulfanyl-thiazol-2-ylamine

(4-Ethylsulfanyl-thiazol-2yl)-carbamic acid tert-butyl ester (0.583 g, 2.24 mmole) was dissolved in methylene chloride (9 mL) and the resulting solution was cooled in an ice-water bath. Trifluoroacetic acid (5 mL) was added dropwise to this solution. The solution was stirred under an argon atmosphere for 3 hours, allowing the cooling bath to slowly warm up. At the conclusion of the reaction, the bath temperature was 12° C. The reaction was concentrated. The residue was redissolved in methylene chloride and concentrated. This was repeated two additional times to remove most of the trifluoroacetic acid. Following the final concentration, the residue was dissolved again in methylene chloride and washed with saturated sodium bicarbonate, water and brine. The organic phase was dried over sodium sulfate and concentrated to yield 4-ethylsulfanyl-thiazol-2-ylamine (0.256 g, 65%).

1. temperaturethe resulting solution was cooled in an ice-water bath
2. temperatureto slowly warm up
3. customAt the conclusion of the reaction
4. customwas 12° C
5. concentrationThe reaction was concentrated
6. dissolutionThe residue was redissolved in methylene chloride
7. concentrationconcentrated
8. customto remove most of the trifluoroacetic acid
9. concentrationconcentration
10. dissolutionthe residue was dissolved again in methylene chloride
11. washwashed with saturated sodium bicarbonate, water and brine
12. dry with materialThe organic phase was dried over sodium sulfate
13. concentrationconcentrated

ORD record

ord-dafbd9d12b564aecb50cf05e1f676174

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07427635B2