Azidobenzene → HCID 57772258, compound

HRID 1645197

Reaction equation

HRID 1645197 reaction equation
[C:1]([O:5][CH2:6][C:7]#[CH:8])(=[O:4])[CH:2]=[CH2:3].[C:9]1([N:15]=[N+:16]=[N-:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN(C=O)C.O>[C:9]1([N:15]2[CH:8]=[C:7]([CH2:6][O:5][C:1](=[O:4])[CH:2]=[CH2:3])[N:17]=[N:16]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 69319AzidobenzeneHCID 82655Propargyl acrylate

Product 1

HCID 57772258HCID 57772258, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Propargyl acrylate (13.5 g, moles), phenyl azide (12.5 g, moles) and tetrakis(acetonitrile)copper (I) hexafluorophosphate (0.84 g, 2.3 mmoles) are dissolved in DMF (100 ml) and stirred at room temperature under nitrogen for 24 hours. The reaction mixture is poured in water and the product is extracted with ethyl acetate. The solvent is distilled under reduced pressure, and mixed with diethyl ether wherefrom the product crystallized as an off-white, crystalline solid (23 g; yield 89%; mp 55-56° C.). 1H NMR (CDCl3, δ ppm) 8.08 (s, 1H), 7.72 (d, 2H), 7.51 (t, 2H), 7.44 (q, qH), 6.48 (d, 1H), 6.17 (q, 1H), 5.88 (d, 1H), 5.50 (s, 2H). 13C NMR (CDCl3, δ ppm) 165.9, 143.4, 136.8, 131.5, 129.7, 128.8, 127.8, 122.1, 120.5, 57.5.

Workup

  1. extractionthe product is extracted with ethyl acetate
  2. distillationThe solvent is distilled under reduced pressure
  3. additionmixed with diethyl ether wherefrom the product
  4. customcrystallized as an off-white, crystalline solid (23 g; yield 89%; mp 55-56° C.)

Sources & evidence

ORD record
ord-ae5f092d18ea4521940072c951c7de78
Source dataset
uspto-grants-2012_02
Patent number
US08124701B2

Linked notes

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