Sodium borohydride → HCID 16756661, compound

To a solution of 3-(4-chlorophenyl)-[1,2,4]thiadiazole-5-carboxylic acid ethyl ester (0.85 g, 3.16 mmol) in EtOH (30 ml) was added sodium borohydride (0.30 g, 7.90 mmol) portion wise. The resulting reaction mixture was stirred at room temperature for 2 h. After the completion of the reaction (TLC monitoring), the reaction mass was cooled to 0° C., quenched it with 10 ml of water and concentrated under vacuum. Added 100 ml water and extracted with ethyl acetate (3×50 ml). The combined organic layer was dried over Na2SO4, filtered and concentrated under vacuum. The crude residue was purified over silica gel (100-200 M, 20% EtOAc-Hexane) to get the desired product (0.53 g, 74%).

1. customThe resulting reaction mixture
2. customAfter the completion of the reaction (TLC monitoring)
3. temperaturethe reaction mass was cooled to 0° C.
4. customquenched it with 10 ml of water
5. concentrationconcentrated under vacuum
6. additionAdded 100 ml water
7. extractionextracted with ethyl acetate (3×50 ml)
8. dry with materialThe combined organic layer was dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated under vacuum
11. customThe crude residue was purified over silica gel (100-200 M, 20% EtOAc-Hexane)

ORD record

ord-32cea47595a54149b0b7f3e12a6db713

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415383B2