反应详情

A mixture of 2.4 gm. (0.01 mole) of N,N'-dicyclohexylthiourea, 3.15 gm. (0.012 mole) of triphenylphosphine, 1.55 gm. (0.01 mole) of carbon tetrachloride, and 1.0 gm. (0.01 mole) of triethylamine in 25 ml. of methylene chloride is stirred for 2.5 hr. at 40°-45°. The reaction mixture is concentrated and the residue extracted several times with hot Skellysolve B. The combined Skellysolve B extracts are cooled to room temperature, filtered and evaporated. The crude N,N'-dicyclohexylcarbodiimide is reacted with 5 ml. of morpholine in 10 ml of tert-butyl alcohol at reflux for 16 hours. The reaction mixture is evaporated, toluene added and concentrated to remove residual morpholine. The residue is partitioned between ether and 10% hydrochloric acid. The acid layer is basified with 20% sodium hydroxide solution, nitrogen bubbled through the solution to remove ether and cooled at 5°. The product is collected, 2.07 gm. (70%), m.p. 105°-107°. The HCl salt is prepared and recrystallized from acetonitrile-ether, m.p. 226°-227°.

1. additionA mixture of 2.4 gm
2. customat 40°-45°
3. concentrationThe reaction mixture is concentrated
4. extractionthe residue extracted several times with hot Skellysolve B
5. filtrationfiltered
6. customevaporated
7. customThe crude N,N'-dicyclohexylcarbodiimide is reacted with 5 ml
8. customThe reaction mixture is evaporated
9. additiontoluene added
10. concentrationconcentrated
11. customto remove residual morpholine
12. customThe residue is partitioned between ether and 10% hydrochloric acid
13. custombubbled through the solution
14. customto remove ether
15. temperaturecooled at 5°
16. customThe product is collected
17. customrecrystallized from acetonitrile-ether, m.p. 226°-227°