Triethylamine → 3,5-Bis(2-hydroxyphenyl)-1-(4-methoxyphenyl)-1H-[1,2,4]triazole

HRID 1358513Notes

Reaction equation

HRID 1358513 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12](=O)[N:13]=1.Cl.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][NH2:29])=[CH:24][CH:23]=1.C(N(CC)CC)C>C(O)C>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([C:11]2[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=2[OH:9])[N:28]([C:25]2[CH:26]=[CH:27][C:22]([O:21][CH3:20])=[CH:23][CH:24]=2)[N:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 1356857232-(2-Hydroxyphenyl)-4H-1,3-benzoxazin-4-one

Product 1

HCID 1358174823,5-Bis(2-hydroxyphenyl)-1-(4-methoxyphenyl)-1H-[1,2,4]triazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5 g of 2-(2-hydroxyphenyl)benz[e][1,3]oxazin-4-one, 3.7 g of 4-methoxyphenylhydrazine hydrochloride and 3 ml of triethylamine are boiled under reflux for 2 h in 75 ml of ethanol. The mixture is cooled, poured onto water and extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated on a rotary evaporator. The residue is crystallized from isopropanol. After drying, 3,5-bis(2-hydroxyphenyl)-1-(4-methoxyphenyl)-1H-[1,2,4]triazole remains as colorless crystals of m.p. 179-181° C.

Workup

  1. temperatureThe mixture is cooled
  2. additionpoured onto water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. concentrationconcentrated on a rotary evaporator
  6. customThe residue is crystallized from isopropanol
  7. customAfter drying

Sources & evidence

ORD record
ord-bf96b85151124801b64af87ce0756e10
Source dataset
uspto-grants-2003_07
Patent number
US06596750B2

Reaction notes

Loading…