Hydrogen Bromide → 4,4'-(3-ethyl-4H-1,2,4-triazol-4,5-diyl)-bis-phenol

HRID 1981173Notes

Reaction equation

HRID 1981173 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=3)[C:12]([CH2:22][CH3:23])=[N:11][N:10]=2)=[CH:5][CH:4]=1.Br>>[CH2:22]([C:12]1[N:13]([C:14]2[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=2)[C:9]([C:6]2[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=2)=[N:10][N:11]=1)[CH3:23]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 130540183,4-bis-(4-methoxyphenyl)-5-ethyl-4H-1,2,4-triazole

Product 1

HCID 1357361654,4'-(3-ethyl-4H-1,2,4-triazol-4,5-diyl)-bis-phenolYield 80.6%

Procedure

A solution of 6 g of 3,4-bis-(4-methoxyphenyl)-5-ethyl-4H-1,2,4-triazole and 25 ml of a solution of hydrobromic acid at 48% was refluxed with stirring for one hour and the hydrobromic acid was distilled under reduced pressure. The crystalline residue was dissolved in 30 ml of hot water and ammonium hydroxide was added thereto until the pH was alkaline. The mixture stood overnight with stirring and was vacuum filtered. The product was washed with water and dried at 90° C. under reduced pressure to obtain a product which was crystallized from dimethylformamide. The mixture was iced for one hour and was vacuum filtered. The product was washed with a 3-4 dimethylformamide-water mixture and dried to obtain 4.395 g of 4,4'-(3-ethyl-4H-1,2,4-triazol-4,5-diyl)-bis-phenol melting at 317°-318° C.

Workup

  1. distillationthe hydrobromic acid was distilled under reduced pressure
  2. dissolutionThe crystalline residue was dissolved in 30 ml of hot water
  3. additionammonium hydroxide was added
  4. waitThe mixture stood overnight
  5. stirringwith stirring
  6. filtrationfiltered
  7. washThe product was washed with water
  8. customdried at 90° C. under reduced pressure
  9. customto obtain a product which
  10. customwas crystallized from dimethylformamide
  11. waitThe mixture was iced for one hour
  12. filtrationfiltered
  13. washThe product was washed with a 3-4 dimethylformamide-water mixture
  14. customdried

Sources & evidence

ORD record
ord-00bbc6091b704d77940feb0e9c54e400
Source dataset
uspto-grants-1985_04
Patent number
US04512997

Reaction notes

Loading…