Triethylamine → HCID 135817486, compound

HRID 1358517Notes

Reaction equation

HRID 1358517 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.[CH2:20]([N:22]([CH2:32][CH3:33])[C:23]1[CH:31]=[CH:30][C:26]([CH2:27][NH:28][NH2:29])=[CH:25][CH:24]=1)[CH3:21].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:28]([CH2:27][C:26]2[CH:30]=[CH:31][C:23]([N:22]([CH2:32][CH3:33])[CH2:20][CH3:21])=[CH:24][CH:25]=2)[N:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22728069HCID 22728069, compoundHCID 1356857232-(2-Hydroxyphenyl)-4H-1,3-benzoxazin-4-one

Product 1

HCID 135817486HCID 135817486, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.0 g of 2-(2-hydroxyphenyl)benz[e][1,3]oxazin-4-one are boiled under reflux for 18 h with 5.4 g of 4-diethylaminobenzylhydrazine hydrochloride and 6.7 ml of triethylamine in 50 ml of ethanol. The mixture is 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-diethylaminobenzyl)-1H-[1,2,4]triazole remains as colorless crystals of m.p. 125-127° C.

Workup

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

Sources & evidence

ORD record
ord-80f9dd4207184f78b457fb6e0246f2c5
Source dataset
uspto-grants-2003_07
Patent number
US06596750B2

Reaction notes

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