反应详情

The Bis(ethylheptylamino)methane (0.95 g, 3.2 mmol) of Preparation 15 in 8 ml of tetrahydrofuran (THF), under nitrogen, is cooled in an ice bath and treated dropwise over 2 min with 0.23 ml (0.25 g, 3.2 mmol) of acetyl chloride; the mixture is stirred 15 min in the cold and 45 min at ambient temperature. The mixture is cooled in an ice bath and a solution of N-(4-acetylphenyl)methanesulfonamide, as described in Preparation 1, (dried by azeotrope from carbon tetrachloride then benzene) (0.68 g, 3.2 mmol) in 10 ml of THF is added dropwise over 5 min. It is stirred in the cold for 1 hr then at room temperature for 72 hrs. The solvent is removed in vacuo (bath <30° C.) and the residue partitioned between cold diluted HCl and ether. The layers are separated and the aqueous layer is extracted with additional ether (4×50 ml). The pooled ether extract is washed with cold diluted HCl. The aqueous layers are combined and brought to pH 8.5 with saturated NaHCO3. This is extracted with ethyl acetate (3×75 ml). The pooled ethyl acetate extract is washed with brine, dried (Na2SO4), acidified with excess ethereal HCl and concentrated to give a mixture which includes the title compound that can be used without further purification.

1. temperatureunder nitrogen, is cooled in an ice bath
2. temperatureThe mixture is cooled in an ice bath
3. dry with material(dried by azeotrope from carbon tetrachloride
4. additionbenzene) (0.68 g, 3.2 mmol) in 10 ml of THF is added dropwise over 5 min
5. stirringIt is stirred in the cold for 1 hr
6. waitat room temperature for 72 hrs
7. customThe solvent is removed in vacuo (bath <30° C.)
8. customthe residue partitioned between cold diluted HCl and ether
9. customThe layers are separated
10. extractionthe aqueous layer is extracted with additional ether (4×50 ml)
11. extractionThe pooled ether extract
12. washis washed with cold diluted HCl
13. extractionThis is extracted with ethyl acetate (3×75 ml)
14. extractionThe pooled ethyl acetate extract
15. washis washed with brine
16. dry with materialdried (Na2SO4)
17. concentrationconcentrated
18. customto give a mixture which