Ethylene Glycol → HCID 9855821, compound

HRID 984597Notes

Reaction equation

HRID 984597 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.I[C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[C:21]#[N:22].C(O)CO>[Cu]I.CCCCCC.C(OCC)(=O)C.CC(O)C>[C:9]([C:10]1[CH:15]=[C:14]([NH:22][CH2:21][C:20]2[CH:23]=[CH:24][CH:25]=[CH:18][CH:19]=2)[CH:13]=[CH:12][CH:11]=1)#[N:16]

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 7504BenzylamineHCID 62657Potassium Phosphate, TribasicHCID 1443413-Iodobenzonitrile

Product 1

HCID 9855821HCID 9855821, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

The general procedure under argon was followed using copper(I) iodide (10 mg, 0.05 mmol), K3PO4 (425 mg, 2.00 mmol), benzylamine (131 μL, 1.20 mmol), 3-iodobenzonitrile (229 mg, 1.00 mmol), ethylene glycol (111 μL, 2.00 mmol) and 2-propanol (1.0 mL). Column chromatography using a solvent mixture (hexane/ethyl acetate=5/1, Rf=0.5) afforded N-(3-cyanophenyl)benzylamine (165 mg, 80% isolated yield) as light yellow solid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity.

Sources & evidence

ORD record
ord-c3177ee910d94cc0967143ee46458a1e
Source dataset
uspto-grants-2005_03
Patent number
US06867298B2

Reaction notes

Loading…