Triethylamine → 5-(Tert-Butyl)-3-(Chloromethyl)-1,2,4-Oxadiazole

Temperature

130 °C

5.0 g of 2-chloro-N-hydroxyacetoamidine and 6.11 g of trimethylacetyl chloride were dissolved in 100 ml of N,N-dimethylformamide, and 5.6 g of triethylamine was then added dropwise under ice-cooling. After completion of the addition, the reaction mixture was stirred at 130° C. for 6 hours and then cooled to room temperature. After aqueous saturated sodium chloride, the reaction mixture was extracted with methyl-t-butyl ether. The organic layer was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 7.0 g of 3-(chloromethyl)-5-t-butyl-1,2,4-oxadiazole.

1. temperaturecooling
2. additionAfter completion of the addition
3. temperaturecooled to room temperature
4. extractionAfter aqueous saturated sodium chloride, the reaction mixture was extracted with methyl-t-butyl ether
5. washThe organic layer was washed with aqueous saturated sodium chloride
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure

ORD record

ord-96b11840e98b478a92b05a067b3babf8

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07846956B2