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

HRID 1358509Notes

Reaction equation

HRID 1358509 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.C(N(CC)CC)C.Cl.[N+:27]([C:30]1[CH:35]=[CH:34][C:33]([NH:36][NH2:37])=[CH:32][CH:31]=1)([O-:29])=[O:28]>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:36]([C:33]2[CH:34]=[CH:35][C:30]([N+:27]([O-:29])=[O:28])=[CH:31][CH:32]=2)[N:37]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 54634014-Nitrophenylhydrazine hydrochlorideHCID 1356857232-(2-Hydroxyphenyl)-4H-1,3-benzoxazin-4-one

Product 1

HCID 1358174923,5-Bis(2-hydroxyphenyl)-1-(4-nitrophenyl)-1H-[1,2,4]triazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.0 g of 2-(2-hydroxyphenyl)benz[e][1,3]oxazin-4-one, 0.5 ml of triethylamine and 0.7 g of 4-nitrophenylhydrazine hydrochloride are boiled under reflux for 1 h in 10 ml of ethanol. On cooling, the product precipitates in crystalline form. It is filtered off and washed with ethanol. After drying, 3,5-bis(2-hydroxyphenyl)-1-(4-nitrophenyl)-1H-[1,2,4]triazole remains as colorless crystals of m.p. 180-183° C.

Workup

  1. temperatureOn cooling
  2. customthe product precipitates in crystalline form
  3. filtrationIt is filtered off
  4. washwashed with ethanol
  5. customAfter drying

Sources & evidence

ORD record
ord-44f008fe48904470b828b0110ede743c
Source dataset
uspto-grants-2003_07
Patent number
US06596750B2

Reaction notes

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