反应详情

To a solution of the amine 7 (prepared above) in 2 mL of dry DMF at 0° C. was added NaH (37 mg, 60% dispersion in mineral oil). The solution was warmed to room temperature for 10 minutes, then recooled to 0° C. 3-Chlorophenylisocyanate (0.084 mL) was added dropwise, and the cooling bath was removed. After three hours, the reaction was poured into EtOAc/hexane (2:1) and water, washed with sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude urea 1 as a yellow foam. Half of this material was purified by silica gel chromatography (3-5% MeOH/CH2Cl2), taken up in CH2Cl2 and treated with 1 M HCl/ether solution, and concentrated in vacuo. The product hydrochloride 1 (75 mg) was isolated as a yellow solid.

1. customrecooled to 0° C
2. customthe cooling bath was removed
3. additionthe reaction was poured into EtOAc/hexane (2:1) and water
4. washwashed with sat. aq. NaHCO3 and brine
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto provide the crude urea 1 as a yellow foam
9. customHalf of this material was purified by silica gel chromatography (3-5% MeOH/CH2Cl2)
10. additiontreated with 1 M HCl/ether solution
11. concentrationconcentrated in vacuo