Sodium Hydroxide → HCID 86613753, compound

Part A: A mixture of 3-ethoxythiophenol (10.0 g, 0.065 mol), 2-amino-5-bromothiazole monohydrobromide (17.7 g, 0.068 mol), 1 M aqueous NaOH (200 mL), and THF (200 mL) was stirred at RT for 15 min. The reaction mixture was warmed to 55° C. over 1 h, cooled to RT and concentrated under reduced pressure to remove THF. The residue was partitioned between EtOAc (ca. 500 mL) and water (ca 100 mL), and the layers were separated. The organic phase was washed with saturated aqueous NaCl (1×200 mL), dried (Na2SO4), and concentrated under reduced pressure to give a solid. The solid was triturated with CH2Cl2:hexanes (ca. 10:1) to provide 5-(3-ethoxy-phenylsulfanyl)-thiazol-2-ylamine (13.2 g, 80%) as a light brown solid. LCMS (m/z): 253 (M+H)+

1. temperatureThe reaction mixture was warmed to 55° C. over 1 h
2. temperaturecooled to RT
3. concentrationconcentrated under reduced pressure
4. customto remove THF
5. customThe residue was partitioned between EtOAc (ca. 500 mL) and water (ca 100 mL)
6. customthe layers were separated
7. washThe organic phase was washed with saturated aqueous NaCl (1×200 mL)
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated under reduced pressure
10. customto give a solid
11. customThe solid was triturated with CH2Cl2

ORD record

ord-ca9ac59a4a23460c95fa88a5579eba21

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08034954B2