Reaktion #1820343

Reaktionsgleichung

hydrochloric acid

4-amino-1-cyclohexylbenzotriazole

hydrochloric acid

sodium nitrite

→

4-chloro-1-cyclohexyl-1H-benzotriazole

Lösungsmittel

water

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat 5° C.
2. 2
   workup.ADDITIONOn completion of the addition
3. 3
   workup.ADDITIONOn completion of the addition
4. 4
   workup.STIRRINGto stir
5. 5
   Sonstigecome to room temperature over a 21
6. 6
   Sonstige2 hour period
7. 7
   Filtrationthe crude product is collected by filtration
8. 8
   Waschenwashed with water and air
9. 9
   Sonstigedried
10. 10
    SonstigeThe product is purified by column chromatography, yield: 6.2 gram, m.p.=141°-144° C
11. 11
    SonstigeThe analytical sample, m.p.=146°-147° C., is recrystallized from CHCl3 /Et2O

Vorschrift

To a stirred solution of 11.4 grams of the 4-amino-1-cyclohexylbenzotriazole in 75 milliliters of concentrated hydrochloric acid and 75 milliliters of water at 5° C. is slowly added 4.1 grams of sodium nitrite in 15 milliliters of water. On completion of the addition, the reaction mixture is allowed to stir an additional 1/2 hour at 0°-5° C. Next the solution is added slowly to an excess of freshly prepared cuprous chloride in 120 milliliters of concentrated hydrochloric acid also at 0°-5° C. On completion of the addition, the reaction is allowed to stir and come to room temperature over a 21/2 hour period. Then 1000 milliliters of water is added to the reaction mixture and the crude product is collected by filtration, washed with water and air dried. The product is purified by column chromatography, yield: 6.2 gram, m.p.=141°-144° C. The analytical sample, m.p.=146°-147° C., is recrystallized from CHCl3 /Et2O.

Quelle