Pivaloyl chloride → HCID 2804877, compound

Temperature

80 °C

To a suspension of 4-methyl-3-thiosemicarbazide (0.53 g) in dichloromethane (10 mL) and triethylamine (0.73 mL) was added slowly via syringe pivaloyl chloride (5 mmol). Formation of a precipitate was observed. The mixture was kept overnight. Volatiles were evaporated in vacuo, the residue heated to 80° C. in aqueous NaOH (1 M, 25 mL) for 3 h. Aqueous HCl (2 M) was then added at 25° C. until pH ca. 6. The mixture was concentrated to dryness, water (10 mL) was added and the product collected by filtration, washing with saturated aqueous NaHCO3 (2.5 mL) and then water (10 mL) to give, after drying, the title compound (0.23 g) of ca. 90% purity by NMR as a colourless solid.

1. customVolatiles were evaporated in vacuo
2. additionAqueous HCl (2 M) was then added at 25° C. until pH ca. 6
3. concentrationThe mixture was concentrated to dryness, water (10 mL)
4. additionwas added
5. filtrationthe product collected by filtration
6. washwashing with saturated aqueous NaHCO3 (2.5 mL)
7. customwater (10 mL) to give
8. customafter drying

ORD record

ord-0c712bcbe8dc40ac9b88a1e41ee87ec9

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07807698B2