N,N'-Dimethylethylenediamine → HCID 5151499, compound

HRID 1883433Notes

Reaction equation

HRID 1883433 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[NH:9]1[CH2:13][CH2:12][NH:11][C:10]1=[O:14].I[C:16]1[CH:17]=[C:18]([O:22][CH3:23])[CH:19]=[CH:20][CH:21]=1.CNCCNC>[Cu]I.CN(C=O)C>[CH3:23][O:22][C:18]1[CH:17]=[C:16]([N:9]2[CH2:13][CH2:12][NH:11][C:10]2=[O:14])[CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 84532-ImidazolidinoneHCID 62657Potassium Phosphate, TribasicHCID 69839Benzene, 1-iodo-3-methoxy-

Product 1

HCID 5151499HCID 5151499, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A microwave test tube was charged with CuI (20 mg, 0.10 mmol, 0.10 equiv), K3PO4 (425 mg, 2.0 mmol, 2.0 equiv), 2-imidazolidone (1.29 g, 15.0 mmol, 15.0 equiv), 3-iodoanisole (119 μL, 1.0 mmol, 1.0 equiv), N,N′-dimethylethylenediamine (22 μL, 0.20 mmol, 0.20 equiv) and dry DMF (2.0 mL), filled with argon. The test tube was sealed and the reaction mixture was stirred at 130° C. for 15 h in the microwave. The resulting suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel, eluting with ethyl acetate. The filtrate was concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (2×20 cm; hexane:ethyl acetate 1:2) provided 128 mg (67% yield) of the title compound as a white solid.

Workup

  1. additionfilled with argon
  2. customThe test tube was sealed
  3. temperatureThe resulting suspension was cooled to room temperature
  4. filtrationfiltered through a 0.5×1 cm pad of silica gel
  5. washeluting with ethyl acetate
  6. concentrationThe filtrate was concentrated in vacuo
  7. customPurification of the residue by flash chromatography on silica gel (2×20 cm; hexane:ethyl acetate 1:2)

Sources & evidence

ORD record
ord-293b2e9fe94c4a2f9b61037f110143bb
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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