Salicylamide → HCID 590558, compound

Salicylamide (40.0 g.) and anhydrous chloral (400 ml.) were heated together on a steam-bath for 3 hours, the reaction mixture was cooled, and the excess of chloral was evaporated under reduced pressure. The syrupy product was mixed with concentrated sulphuric acid (500 ml.) and heated on a steam-bath for 1 hour. The mixture was cooled and poured into crushed ice (3 kg.), and the precipitated solid was filtered off, triturated with diethyl ether (300 ml.) and filtered again. The solid product was stirred with water (1 l.), filtered, washed well with water, dried and crystallised from ethanol (400 ml.) to yield 3,4-dihydro-2-trichloromethyl-2H-benzo[e]-[1,3]-oxazin-4-one, m.p. 175°-177° C.

1. temperaturethe reaction mixture was cooled
2. customthe excess of chloral was evaporated under reduced pressure
3. additionThe syrupy product was mixed with concentrated sulphuric acid (500 ml.)
4. temperatureheated on a steam-bath for 1 hour
5. temperatureThe mixture was cooled
6. additionpoured
7. custominto crushed ice (3 kg.)
8. filtrationthe precipitated solid was filtered off
9. customtriturated with diethyl ether (300 ml.)
10. filtrationfiltered again
11. filtrationfiltered
12. washwashed well with water
13. customdried
14. customcrystallised from ethanol (400 ml.)

ORD record

ord-3eac59e60a5d4285a13c5055bf8492bf

Source dataset

uspto-grants-1981_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04268510