Water → HCID 617437, compound

Temperature

135 °C

Into a 50-mL round-bottom flask, was placed 3-chloro-5-phenyl-1,2-thiazole-4-carbonitrile (700 mg, 3.01 mmol, 1.00 equiv, 95%), con.H2SO4 (4 mL). The resulting solution was stirred for 3 hr at 135° C. in an oil bath. This was followed by the addition of a solution of NaNO2 (318 mg, 4.61 mmol, 1.45 equiv) in water (15 mL) dropwise with stirring at 0° C. The resulting solution was allowed to react, with stirring, for an additional 0.5 h while the temperature was maintained at 50° C. in an oil bath. The resulting solution was extracted with 3×20 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2×50 mL of sodium hydroxide/H2O(10%). The resulting solution was extracted with 3×100 mL of ethyl acetate. The aqueous phase was adjusted to 3 with 2N HCl. The resulting solution was extracted with 3×100 mL of ethyl acetate and the organic layers combined and concentrated under vacuum. This resulted in 500 mg (66%) of 3-chloro-5-phenyl-1,2-thiazole-4-carboxylic acid as a white solid.

1. customInto a 50-mL round-bottom flask, was placed
2. stirringwith stirring at 0° C
3. customto react
4. stirringwith stirring, for an additional 0.5 h while the temperature
5. temperaturewas maintained at 50° C. in an oil bath
6. extractionThe resulting solution was extracted with 3×20 mL of ethyl acetate
7. washThe resulting mixture was washed with 2×50 mL of sodium hydroxide/H2O(10%)
8. extractionThe resulting solution was extracted with 3×100 mL of ethyl acetate
9. extractionThe resulting solution was extracted with 3×100 mL of ethyl acetate
10. concentrationconcentrated under vacuum
11. customThis resulted in 500 mg (66%) of 3-chloro-5-phenyl-1,2-thiazole-4-carboxylic acid as a white solid

ORD record

ord-2fa795f2be7c49a599131c448620a0fd

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1