Reaktion #2170813

Reaktionsgleichung

4-amino-1-cyclohexylbenzotriazole

hydrochloric acid

sodium nitrite

hydrochloric acid

→

4-Chloro-1-cyclohexyl-1H-benzotriazole

Lösungsmittel

water

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigekept at 5° C.
2. 2
   workup.ADDITIONOn completion of the addition
3. 3
   Sonstigealso at 0°-5° C
4. 4
   workup.ADDITIONOn completion of the addition
5. 5
   workup.STIRRINGto stir
6. 6
   Sonstigecome to room temperature over a 21
7. 7
   Sonstige2 hour period
8. 8
   Filtrationthe crude product is collected by filtration
9. 9
   Waschenwashed with water and air
10. 10
    Sonstigedried
11. 11
    SonstigeThe product is purified by column chromatography, yield: 6.2 g, m.p. = 141°-144° C, analytical sample, m.p.=146°-147° C.
12. 12
    Sonstigeis recrystallized from CHCl3 /Et2O

Vorschrift

To a stirred solution of 11.4 g. of the 4-amino-1-cyclohexylbenzotriazole in 75 ml. of concentrated hydrochloric acid and 75 ml. of water kept at 5° C. is slowly added 4.1 g. of sodium nitrite in 15 ml. of water. On completion of the addition, the reaction mixture is allowed to stir an additional 1/2 hour at 0°-5° C. and then is added slowly to an excess of freshly prepared cuprous chloride in 120 ml. 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 ml. 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 g, m.p. = 141°-144° C, analytical sample, m.p.=146°-147° C., is recrystallized from CHCl3 /Et2O.

Quelle