Hydrazoic acid → 5-(chloromethyl)-1-cyclohexyl-1H-tetrazole

Into 150 ml of dried benzene, 17.6 g of N-chloroacetylcyclohexylamine was added. While the inside temperature is kept below 15° C. by ice-cooling the outside of the reaction vessel, 24 g of phosphorus pentachloride (PCl5) was added under stirring condition. After completion of the addition, the stirring is continued for 2 hours at a room temperature, then the reaction mixture is concentrated to a half volume thereof by using an evaporator with a bath temperature of below 50° C. To the concentrated reaction mixture was added dropwise 100 ml of benzene containing 10% of HN3 under stirring condition for 90 minutes while keeping the inside temperature below 15° C. After the addition operation, the reaction mixture is allowed to stand overnight. Then the reaction mixture is refluxed for 3 hours with stirring. The thus obtained concentrate is extracted with 200 ml of chloroform. The chloroform layer is washed with water, 5% NaHCO3 aqueous solution, 5% hydrochloric acid and water in this order and dried with Na2SO4. After removal of the drying agent by filtration, the mother liquour is concentrated and the residue thus obtained is recrystallized from chloroform-petroleum ether to obtain 16.1 g of 1-cyclohexyl-5-chloromethyltetrazol in the form of colorless needle like crystals. Melting point: 101° to 103.5° C.

1. customis kept below 15° C. by ice-
2. additionwas added
3. additionAfter completion of the addition
4. concentrationthe reaction mixture is concentrated to a half volume
5. customan evaporator with a bath temperature of below 50° C
6. customTo the concentrated reaction mixture
7. stirringunder stirring condition for 90 minutes
8. customthe inside temperature below 15° C
9. waitto stand overnight
10. temperatureThen the reaction mixture is refluxed for 3 hours
11. stirringwith stirring
12. customThe thus obtained
13. concentrationconcentrate
14. extractionis extracted with 200 ml of chloroform
15. washThe chloroform layer is washed with water, 5% NaHCO3 aqueous solution, 5% hydrochloric acid and water in this order
16. dry with materialdried with Na2SO4
17. customAfter removal of the drying agent
18. filtrationby filtration
19. concentrationthe mother liquour is concentrated
20. customthe residue thus obtained
21. customis recrystallized from chloroform-petroleum ether

ORD record

ord-e292b5a48aaa4521b4f883103049e2c7

Source dataset

uspto-grants-1981_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04277479