Methanol → 5-(5-Bromo-furan-2-yl)-[1,3,4]oxadiazole-2-thiol

5-Bromo-furan-2-carboxylic acid hydrazide (20.5 g, 100 mmol) was added to a mixture of potassium hydroxide (6.2 g, 110 mmol) and methanol (125 ml). The mixture was stirred for 30 minutes at room temperature. Carbon disulfide (15.2 g, 200 mmol) was added. The mixture was stirred at reflux for 30 hours. Water (60 ml) was added and the excess of carbon disulfide and methanol was evaporated. The aqueous suspension was acidified by adding concentrated hydrochloric acid (14 ml). The product precipitated and was washed with water (20 ml), dried and evaporated. Yield 8.58 g (35%).

1. stirringThe mixture was stirred
2. temperatureat reflux for 30 hours
3. customthe excess of carbon disulfide and methanol was evaporated
4. additionby adding concentrated hydrochloric acid (14 ml)
5. customThe product precipitated
6. washwas washed with water (20 ml)
7. customdried
8. customevaporated

ORD record

ord-4f18b1e964144ee0bc28831be636126e

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08372832B2