Réaction #214423

Équation de réaction

1,5-naphthalenedisulphonic acid

1-bromo-4-chloro-1-[4-(4-chlorophenyl)-phenoxy]-3,3-dimethyl-butan-2-one

imidazole

→

4-chloro-1-[4-(4-chlorophenyl)-phenoxy]-3,3-dimethyl-1(imidazol-1-yl)-butan-2-one naphthalene-1,5-disulphonate

Rendement 74.6%

Solvants

acetone

acetonitrile

Conditions de réaction

Traitement

1. 1
   Températurethe mixture was heated for 40 hours
2. 2
   Températureunder reflux
3. 3
   ConcentrationIt was then concentrated
4. 4
   workup.DISTILLATIONby distilling off the solvent in vacuo
5. 5
   LavageThe solution was washed three times with 100 ml of water at a time
6. 6
   Séchagewas dried over sodium sulphate
7. 7
   Concentrationagain concentrated in vacuo
8. 8
   Autrethe precipitate formed
9. 9
   Filtrationwas filtered off
10. 10
    Autredried

Mode opératoire

20.8 g (0.05 mol) of crude 1-bromo-4-chloro-1-[4-(4-chlorophenyl)-phenoxy]-3,3-dimethyl-butan-2-one were dissolved in 120 ml of absolute acetonitrile. 12 g (0.175 mol) of imidazole were added and the mixture was heated for 40 hours under reflux. It was then concentrated by distilling off the solvent in vacuo and the residue was taken up in 300 ml of methylene chloride. The solution was washed three times with 100 ml of water at a time and was dried over sodium sulphate and again concentrated in vacuo. The residue was taken up in 100 ml of acetone and a solution of 9 g (0.038 mol) of 1,5-naphthalenedisulphonic acid in 50 ml of acetone was added. After 2 hours, the precipitate formed was filtered off and dried. 19.6 g (72% of theory) of 4-chloro-1-[4-(4-chlorophenyl)-phenoxy]-3,3-dimethyl-1(imidazol-1-yl)-butan-2-one naphthalene-1,5-disulphonate of melting point 246° C. were obtained.

Source