Water → 1-Hexadecyl-4-acryloyloxymethyl-triazole

HRID 1645196Notes

Reaction equation

HRID 1645196 reaction equation
[C:1]([O:5][CH2:6][C:7]#[CH:8])(=[O:4])[CH:2]=[CH2:3].[CH2:9]([N:25]=[N+:26]=[N-:27])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].O>CN(C=O)C>[CH2:9]([N:25]1[CH:8]=[C:7]([CH2:6][O:5][C:1](=[O:4])[CH:2]=[CH2:3])[N:27]=[N:26]1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 82655Propargyl acrylateHCID 11230945Hexadecyl azide

Product 1

HCID 577722611-Hexadecyl-4-acryloyloxymethyl-triazoleYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Propargyl acrylate (1.10 g, 10 mmoles), hexadecyl azide (2.37 g, 10 mmoles) and tetrakis(acetonitrile)copper (I) hexafluorophosphate (74 mg, 0.2 mmoles) are dissolved in DMF (20 ml) and stirred at room temperature under nitrogen for 24 hours. The reaction mixture is poured into water wherefrom the product precipitated as a white crystalline solid (2.95 g; yield 85%; mp 72-73° C.). 1H NMR (CDCl3, δ ppm) 7.61 (s, 1H), 6.44 (d, 1H), 6.14 (dd, 1H), 5.85 (d, 1H), 5.31 (s, 2H), 4.34 (t, 2H), 1.92 (q, 2H), 1.26 (m, 28H), 0.88 (t, 3H). 13C NMR (CDCl3, δ ppm) 166.00, 142.73, 131.39, 128.04, 123.64, 57.75, 50.43, 31.89, 30.22, 29.66, 29.65, 29.64, 29.62, 29.61, 29.56, 29.47, 29.33, 29.32, 28.95, 26.46, 22.66, 14.08. MS for C12H39N3O2 calculated 377.58; found 377.20.

Workup

  1. customprecipitated as a white crystalline solid (2.95 g; yield 85%; mp 72-73° C.)

Sources & evidence

ORD record
ord-c845d86b7ad2470cb2ba6c7ce3354337
Source dataset
uspto-grants-2012_02
Patent number
US08124701B2

Reaction notes

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