Triethylamine → HCID 135817486, compound

HRID 991716Notes

Reaction equation

HRID 991716 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-9b76743c452e4919a7ed62e46bd7ca95
Source dataset
uspto-grants-2002_10
Patent number
US06465504B1

Reaction notes

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