Triethylamine → HCID 14477033, compound

To a solution of 17.1 grams (g) (0.1 mole) of (2-chlorophenyl) acetic acid in 100 milliliters (ml) of dichloromethane and 0.5 ml of dimethylformamide was added 19.0 g (0.15 mole) of oxalyl chloride dropwise over a 30 minute period. Evolution of gas commenced and lasted for approximately 30 minutes, after which the excess liquids were removed in vacuo. To the residue was added 100 milliliters (ml) of acetonitrile and 12.0 g (0.1 mole) of zinc cyanide, and the mixture was stirred for 15 minutes at room temperature. Thereafter, 11.2 g (0.1 mole) of 1,3-cyclohexanedione was added, followed by the dropwise addition of 15.0 g (0.148 mole) of triethylamine over a five minute period. The exothermic reaction reached approximately 50° C., after which it subsided. The mixture was heated at reflux for approximately one hour, then cooled to room temperature and the acetonitrile was removed in vacuo. To the residue was added 2N hydrogen chloride (to decompose the zinc salts), and ethyl ether. The various layers were separated, and the organic layer was washed with 5% potassium carbonate. The aqueous layer was acidified and extracted with dichloromethane three times. The dichloromethane layer was dried over magnesium sulfate, and the excess dichloromethane was roto-evaporated off. The crude product that was obtained was then stirred with a 5% Cu(OAc)2 solution. The blue copper complex that resulted was filtered, and then decomposed with 6N HCl. The acidic solution was extracted with dichloromethane. After drying over MgSO4, the dichloromethane was removed in vacuo to afford 1.2 g of a brown semi-solid which was identified as the subject compound.

1. customafter which the excess liquids were removed in vacuo
2. customThe exothermic reaction
3. customreached approximately 50° C.
4. temperatureThe mixture was heated
5. temperatureat reflux for approximately one hour
6. temperaturecooled to room temperature
7. customthe acetonitrile was removed in vacuo
8. additionTo the residue was added 2N hydrogen chloride (
9. customThe various layers were separated
10. washthe organic layer was washed with 5% potassium carbonate
11. extractionextracted with dichloromethane three times
12. dry with materialThe dichloromethane layer was dried over magnesium sulfate
13. customthe excess dichloromethane was roto-evaporated off
14. customThe crude product that was obtained
15. customThe blue copper complex that resulted
16. filtrationwas filtered
17. extractionThe acidic solution was extracted with dichloromethane
18. dry with materialAfter drying over MgSO4
19. customthe dichloromethane was removed in vacuo

ORD record

ord-5eb075d747714798bea55dac690ed571

Source dataset

uspto-grants-1989_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04822905