N,N'-Dimethylethylenediamine → HCID 20740841, compound

HRID 1883434Notes

Reaction equation

HRID 1883434 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:9][O:10][C:11]1[CH:12]=[C:13]([N:17]2[CH2:21][CH2:20][NH:19][C:18]2=[O:22])[CH:14]=[CH:15][CH:16]=1.[CH3:23][C:24]1[CH:25]=[C:26](I)[CH:27]=[C:28]([CH3:30])[CH:29]=1.CNCCNC>[Cu]I.CN(C=O)C>[CH3:9][O:10][C:11]1[CH:12]=[C:13]([N:17]2[CH2:21][CH2:20][N:19]([C:26]3[CH:27]=[C:28]([CH3:30])[CH:29]=[C:24]([CH3:23])[CH:25]=3)[C:18]2=[O:22])[CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 1409241-Iodo-3,5-dimethylbenzeneHCID 5151499HCID 5151499, compound

Product 1

HCID 20740841HCID 20740841, compoundYield 91%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
160 °C

Procedure

A microwave test tube was charged with CuI (20 mg, 0.10 mmol, 0.20 equiv), K3PO4 (212 mg, 1.0 mmol, 2.0 equiv), N-(3-methoxyphenyl)-2-imidazolidone (96 mg, 0.5 mmol, 1.0 equiv), 3,5-dimethyliodobenzene (144 μL, 1.0 mmol, 2.0 equiv), N,N′-dimethylethylendiamine (22 μL, 0.20 mmol, 0.40 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 and at 160° C. for further 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 4:1) provided 134 mg (91% 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 4:1)

Sources & evidence

ORD record
ord-8bcca66e4b8440c0a82b2f8025a40bc3
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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