Phenyl chloroformate → HCID 18928232, compound

Temperature

-25 °C

A solution of cuprous iodide (0.40 g, 2 mmol) in dry THF (50 ml) was stirred under nitrogen for 10 min. A solution of 3-(3-chloro-1,2,5-thiadiazol-4-yl)pyridine (J.Med.Chem. 1992, 35, 2274-2283) (9.9 g, 50 mmol) in dry THF (150 ml) was added to the reaction, then cooled to -25° C. Phenylchloroformate (6.3 ml, 50 mmol) in THF (20 ml) was added slowly. The reaction mixture was stirred at -25° C. for 30 min., then allowed to warm to room temperature and stirred for another 2.5 h. The reaction mixture was cooled to -25° C. and methylmagnesium iodide (55 mmol in 20 ml ether) was added. The reaction mixture was stirred for 20 min., 20% NH4Cl(aq) (100 ml) was added and then extracted with ether (200 ml). The combined organic phases were washed with 20% NH4Claq :NH4OH (1:1) (50 ml), water (50 ml), 4N HCl (50 ml), water (50 ml) and brine (50 ml). The organic phases were dried and evaporated to give crude title compound. Purification on column chromatography, eluent: toluene, gave the title compound in 11.9 g (71%) yield.

1. temperatureto warm to room temperature
2. stirringstirred for another 2.5 h
3. temperatureThe reaction mixture was cooled to -25° C.
4. stirringThe reaction mixture was stirred for 20 min.
5. extractionextracted with ether (200 ml)
6. washThe combined organic phases were washed with 20% NH4Claq
7. customThe organic phases were dried
8. customevaporated
9. customto give crude title compound
10. customPurification on column chromatography, eluent

ORD record

ord-8895ac1867a144e688913d18474d7429

Source dataset

uspto-grants-1998_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05741788