Triethylamine → Ethyl [3,5bis(2-hydroxyphenyl)-[1,2,4]triazol-1-yl]acetate

HRID 1358507Notes

Reaction equation

HRID 1358507 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.[NH:27]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[NH2:28]>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:27]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[N:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11593468Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1)HCID 1356857232-(2-Hydroxyphenyl)-4H-1,3-benzoxazin-4-one

Product 1

HCID 135914986Ethyl [3,5bis(2-hydroxyphenyl)-[1,2,4]triazol-1-yl]acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

51.5 g of 2-(2-hydroxyphenyl)benz[e][1,3]oxazin-4-one, 30.5 ml of triethylamine and 33.4 g of ethyl hydrazinoacetate hydrochloride are boiled under reflux for 0.5 h in 450 ml of ethanol. On cooling, the product precipitates in crystalline form. It is filtered off and washed with ethanol. After drying, ethyl [3,5-bis(2-hydroxyphenyl)-[1,2,4]triazol-1-yl]acetate remains as colorless crystals of m.p. 172-174° 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-4371dfd208cd488ba53ecf662bf5bf9b
Source dataset
uspto-grants-2003_07
Patent number
US06596750B2

Reaction notes

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