Ethylene Glycol → Benzylaniline

HRID 984698Notes

Reaction equation

HRID 984698 reaction equation
[CH2:1]([NH:8][C:9](=O)[C:10](F)(F)F)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].I[C:24]1[CH:29]=CC=[CH:26][CH:25]=1.C(O)CO.CCCCCCCCCCCC.N>C(OCC)(=O)C.[Cu]I.C(O)(C)C>[C:9]1([NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]=[CH:26][CH:25]=[CH:24][CH:29]=1

Participants

10

Reactant 6

HCID 174Ethylene GlycolHCID 222AmmoniaHCID 8182DodecaneHCID 11575IodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 230121N-Benzyl-2,2,2-trifluoroethanimidic acid

Product 1

HCID 66028BenzylanilineYield 76%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
80 °C

Procedure

A Schlenk tube was charged with CuI (9.6 mg, 0.050 mmol, 5.0 mol %), N-benzyl-trifluoroacetamide (244 mg, 1.20 mmol), K3PO4 (640 mg, 3.01 mmol), evacuated, backfilled with Ar. Iodobenzene (112 μL, 1.00 mmol), ethylene glycol (0.11 mL, 2.0 mmol), and isopropanol (1.5 mL) were added under Ar. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 80° C. for 24 h. The resulting white suspension was allowed to reach room temperature. Dodecane (internal GC standard, 230 μL), ethyl acetate (2 mL), and 30% aq ammonia (2 mL) were added. A 0.1 mL sample of the top layer was diluted with ethyl acetate (1 mL) and analyzed by GC to provide a 76% yield of N-phenylbenzylamine.

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed with a Teflon valve
  3. customto reach room temperature

Sources & evidence

ORD record
ord-b122decbaa6a485aa2e8243b8a81bd10
Source dataset
uspto-grants-2005_03
Patent number
US06867298B2

Reaction notes

Loading…