Réaction #1262

Équation de réaction

4-chloro-2,6-diaminopyrimidine

sodium acetate

4-chlorobenzenediazonium chloride

→

6-chloro-5-[(4-chlorophenyl)azo]-2,4-pyrimidinediamine

Rendement 41.4%

Solvants

water

acetic acid

Conditions de réaction

Traitement

1. 1
   Températurewith cooling over 30 minutes at a rate that
2. 2
   Autrethe reaction at 18°
3. 3
   workup.STIRRINGThe reaction was stirred overnight at room temperature
4. 4
   Filtrationthe orange crystals were filtered
5. 5
   Lavagewashed with water (4×400 ml)
6. 6
   Autredried in vacuo

Mode opératoire

To a suspension of 4-chloro-2,6-diaminopyrimidine (21.68 g, 0.150 mol) in water (750 ml) and acetic acid (750 ml) was added sodium acetate (300 g). Solution occurred after stirring for 20 minutes, and then the solution of 4-chlorobenzenediazonium chloride (0.166 mol) was added with cooling over 30 minutes at a rate that kept the reaction at 18°. The reaction was stirred overnight at room temperature, and the orange crystals were filtered, washed with water (4×400 ml), and dried in vacuo to give 17.6 g of 6-chloro-5-[(4-chlorophenyl)azo]-2,4-pyrimidinediamine. The mother liquors were cooled to 5° for 20 hours, and the crystals were collected and dried in vacuo to give 6.94 g of additional 6-chloro-5-[(4-chlorophenyl)azo]-2,4-pyrimidineadiamine.

Source