Ethylene Glycol → Diphenylamine

HRID 2179206Notes

Reaction equation

HRID 2179206 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.I[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O)CO>[Cu]I.CCCCCC.C(OCC)(=O)C.CC(O)C>[C:10]1([NH:9][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 6115AnilineHCID 11575IodobenzeneHCID 62657Potassium Phosphate, Tribasic

Product 1

HCID 11487DiphenylamineYield 41%

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), aniline (109 μL, 1.20 mmol), iodobenzene (112 μL, 1.00 mmol), ethylene glycol (111 μL, 2.00 mmol) and 2-propanol (1.0 mL) at 90° C. Column chromatography using a solvent mixture (hexane/ethyl acetate=5/1, Rf=0.4) afforded N-(phenyl)aniline (69 mg, 41% isolated yield) as light yellow solid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity.

Workup

  1. customat 90° C

Sources & evidence

ORD record
ord-20f8567112c54247afa8becc27127251
Source dataset
uspto-grants-2015_06
Patent number
US09067955B2

Reaction notes

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