Ethanol → N-{2-[Bis(2-hydroxyethyl)amino]ethyl}-2-[3,5-bis(2-hydroxyphenyl)-[1,2,4]triazol-1-yl]acetamide

HRID 1358532Notes

Reaction equation

HRID 1358532 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[N:10]([CH2:20][C:21](OCC)=[O:22])[N:9]=1.OCC[NH:29][CH2:30][CH2:31][NH:32][CH2:33][CH2:34][OH:35].[CH2:36]([OH:38])[CH3:37]>>[OH:38][CH2:36][CH2:37][N:32]([CH2:33][CH2:34][OH:35])[CH2:31][CH2:30][NH:29][C:21](=[O:22])[CH2:20][N:10]1[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])=[N:12][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[OH:1])=[N:9]1

Participants

4

Reactant 3

HCID 702EthanolHCID 78179Ethanol, 2,2'-(1,2-ethanediyldiimino)bis-HCID 135914986Ethyl [3,5bis(2-hydroxyphenyl)-[1,2,4]triazol-1-yl]acetate

Product 1

HCID 135817481N-{2-[Bis(2-hydroxyethyl)amino]ethyl}-2-[3,5-bis(2-hydroxyphenyl)-[1,2,4]triazol-1-yl]acetamide

Procedure

2.0 g of ethyl [3,5-bis(2-hydroxyphenyl)-[1,2,4]triazol-1-yl]acetate (Example 2) and 1.0 g of bis(2-hydroxyethyl)ethylenediamine are boiled under reflux for 24 h in 8 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 chromatographed on silica gel. After concentration and drying, N-{2-[bis(2-hydroxyethyl)amino]ethyl}-2-[3,5-bis(2-hydroxyphenyl)-[1,2,4]triazol-1-yl]acetamide remains as a colorless foam. Rf value: 0.35 (silica gel 60, methylene chloride/methanol=9/1). 1H-NMR (DMSO-d6): 2.5 (m, 6H), 3.1 (m, 2H), 3.4 (m, 4H), 4.2 (bs, 2H), 4.9 (s, 2H), 7.0 (m, 4H), 7.4 (m, 3H), 7.95 (d, 1H), 8.1 (t, 1H), 11.0 ppm (s, 1H).

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 chromatographed on silica gel
  7. concentrationAfter concentration
  8. customdrying

Sources & evidence

ORD record
ord-d0105334929d42f28565c3a1c28bc6d8
Source dataset
uspto-grants-2003_07
Patent number
US06596750B2

Reaction notes

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