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

HRID 991717Notes

Reaction equation

HRID 991717 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.[NH:20]([CH2:22][C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1)[NH2:21].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:20]([CH2:22][C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[N:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22728080HCID 22728080, compoundHCID 1356857232-(2-Hydroxyphenyl)-4H-1,3-benzoxazin-4-one

Product 1

HCID 1358174753,5-Bis(2-hydroxyphenyl)-1-(pyridin-4-ylmethyl)-1H-[1,2,4]triazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.0 g of 2-(2-hydroxyphenyl)benz[e][1,3]oxazin4-one are boiled under reflux for 4 h with 5.9 g 4-hydrazinomethylpyridine hydrochloride in [CAS-Reg. No.: 89598-56-1] and 10 ml of triethylamine in 50 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-(pyridin4-ylmethyl)-1H-[1,2,4]triazole remains as colorless crystals of m.p. 197-199° 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-f08716b3b7cb4cb3b5131586d6846dda
Source dataset
uspto-grants-2002_10
Patent number
US06465504B1

Reaction notes

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