Toluene → Dezinamide

To a solution of 2.2 g (0.01 mole) of 3-[3-(trifluoromethyl)phenoxy]azetidine in 45 ml of methylene chloride and 45 ml of absolute ethyl alcohol was added 7 g. (0.066 mole) of nitrourea and the mixture was stirred at room temperature for 48 hr. The mixture was filtered. The filtrate was evaporated to dryness and the residue was partitioned between 75 ml methylene chloride and 75 ml water. The water layer was extracted three times with 50 ml of methylene chloride. The methylene chloride extracts were combined and evaporated to dryness. The residue was treated (washed) with a mixture of 1 ml methylene chloride and 20 ml of toluene and filtered. The precipitate was recrystallized from ethanol-water to give pale yellow crystals. The crystals were mixed with 2 ml of methylene chloride and 20 ml toluene and the mixture was heated on a steam bath for 2 hrs. The mixture was stored in a refrigerator for approximately 72 hrs. and filtered to give 1.2 g of the product as white crystalline needles, m.p. 151°-152° C.

1. filtrationThe mixture was filtered
2. customThe filtrate was evaporated to dryness
3. customthe residue was partitioned between 75 ml methylene chloride and 75 ml water
4. extractionThe water layer was extracted three times with 50 ml of methylene chloride
5. customevaporated to dryness
6. additionThe residue was treated
7. wash(washed)
8. additionwith a mixture of 1 ml methylene chloride and 20 ml of toluene
9. filtrationfiltered
10. customThe precipitate was recrystallized from ethanol-water
11. customto give pale yellow crystals
12. temperaturethe mixture was heated on a steam bath for 2 hrs
13. filtrationand filtered

ORDレコード

ord-10b4cc85505b4271b511d11c03d96fc5

出典データセット

uspto-grants-1986_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04571393