Hydrochloric Acid → HCID 178477521, compound

In a 100 mL round bottomed flask were placed ethyl 2-bromo-4-(4-chlorobenzyl)-1,3-thiazole-5-carboxylate (955 mg, 2.65 mmol) and tetrahydrofuran (50 mL, 600 mmol). To this solution was added a freshly prepared aqueous solution of lithium hydroxide [(lithium hydroxide.H2O (177 mg, 4.22 mmol) and water (15 mL, 830 mmol)). The mixture was stirred for 4 h at rt then MeOH (20 mL) was added and the mixture was refluxed for 3 h. The mixture was allowed to cool to rt and then acidified by the addition of 1.0N HCl aq (4.5 mL). The mixture was stirred for 1 h at rt. The mixture was then concentrated under reduced pressure until reduced to ca 5 mL volume. EtOAc (50 mL) was added and the mixture was washed with water (50 mL), then brine (50 mL), then was dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The residual yellow crystalline solid was used in the next step without further purification. LC/MS (FA) ES+ 332.

1. customIn a 100 mL round bottomed flask were placed
2. temperaturethe mixture was refluxed for 3 h
3. temperatureto cool to rt
4. stirringThe mixture was stirred for 1 h at rt
5. concentrationThe mixture was then concentrated under reduced pressure
6. additionEtOAc (50 mL) was added
7. washthe mixture was washed with water (50 mL)
8. dry with materialbrine (50 mL), then was dried over anhydrous MgSO4
9. customInsoluble materials were removed by filtration
10. concentrationthe filtrate was concentrated under reduced pressure
11. customThe residual yellow crystalline solid was used in the next step without further purification

ORD record

ord-849c4a3f13ee45ecbeb984fcfc76c23b

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796271B2