Ammonia → Dezinamide

A 16 ml solution containing 5.94 g of phosgene was prepared by dissolving phosgene gas in cold toluene. This solution was stirred with 7 g potassium carbonate in an acetone-ice bath for about 10 minutes. To this solution in the bath was added dropwise over a 13 minute period at -9° C. to +4° C. a solution of 19.2 g (0.050 mole) of 1-(diphenylmethyl)-3-[3-(trifluoromethyl)phenoxy]azetidine in 38.4 ml of toluene. The cold bath was removed and the temperature of the reaction mixture rose to 18° C. after 1/2 hr. TLC (silica gel eluted with methylene chloride) of a sample indicated all the 1-(diphenylmethyl)-3-[3-(trifluoromethyl)phenoxy]azetidine had disappeared (reacted). After 1 hr, the mixture was filtered to remove solid, leaving a filtrate containing 3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbonyl chloride and diphenylchloromethane. The filtrate was added (over a 7 min period) to about 30 ml of liquid ammonia at - 60° to -30° C. Some white solid formed in the mixture. The ammonia was refluxed under a dry ice-acetone condenser for 1/2 hr and then allowed to evaporate using nitrogen gas to facilitate the removal of ammonia. Petroleum ether (60 ml) was added to the mixture and the resulting white solid was collected by filtration and rinsed twice with petroleum ether to give 18.1 g of solid. The solid was stirred in 90 ml of water at room temperature for one hr, filtered off, rinsed twice with water and dried under vacuum at about 60° C. for 2 hr to give 13 g (100%) of title compound.

1. customwas prepared
2. customThe cold bath was removed
3. washTLC (silica gel eluted with methylene chloride) of a sample
4. custom(reacted)
5. waitAfter 1 hr
6. filtrationthe mixture was filtered
7. customto remove solid
8. customleaving a filtrate
9. customSome white solid formed in the mixture
10. customto evaporate
11. customthe removal of ammonia
12. additionPetroleum ether (60 ml) was added to the mixture
13. filtrationthe resulting white solid was collected by filtration
14. washrinsed twice with petroleum ether

ORDレコード

ord-d892c5c016a1416e81ab8a1a2a1673e9

出典データセット

uspto-grants-1991_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05068231