N,N'-Dimethylethylenediamine → HCID 21940667, compound

HRID 1883436Notes

Reaction equation

HRID 1883436 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:9]([NH:16][C:17]([NH2:19])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Br[C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24].CNCCNC>[Cu]I.O1CCOCC1>[CH2:9]([NH:16][C:17]([NH:19][C:21]1[CH:27]=[CH:26][CH:25]=[C:23]([NH2:24])[CH:22]=1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 10853BenzylureaHCID 115623-BromoanilineHCID 62657Potassium Phosphate, Tribasic

Product 1

HCID 21940667HCID 21940667, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A test tube was charged with CuI (20 mg, 0.10 mmol, 0.10 equiv), K3PO4 (425 mg, 2.0 mmol, 2.0 equiv), benzylurea (225 mg, 1.5 mmol, 1.5 equiv), 3-bromoaniline (109 μL, 1.0 mmol, 1.0 equiv), N,N′-dimethylethylendiamine (22 μL, 0.20 mmol, 0.20 equiv) and dry dioxane (1.0 mL), filled with nitrogen. The test tube was sealed and the reaction mixture was stirred at 80° C. for 24 h. 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. The solid residue was dissolved in ˜2 mL DMF. Purification of the residue by flash chromatography on silica gel (2×20 cm; hexane:ethyl acetate 1:2) provided 185 mg (77% yield) of the title compound as a light yellow solid.

Workup

  1. additionfilled with nitrogen
  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. dissolutionThe solid residue was dissolved in ˜2 mL DMF
  8. customPurification of the residue by flash chromatography on silica gel (2×20 cm; hexane:ethyl acetate 1:2)

Sources & evidence

ORD record
ord-3d673a7ac93e4c61b7480ccb4517eda3
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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