Ethylenediamine → HCID 68815111, compound

HRID 732535Notes

Reaction equation

HRID 732535 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:16]=[C:15](I)[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.[NH:19]1[CH2:23][CH2:22][CH2:21][C:20]1=[O:24].C(N)CN.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.ClCCl.[Cu]I>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:16]=[C:15]([N:19]2[CH2:23][CH2:22][CH2:21][C:20]2=[O:24])[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1

Participants

8

Reactant 4

HCID 3301EthylenediamineHCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 21086185Methyl 3-iodo-5-{[methyl(propyl)amino]carbonyl}benzoate

Product 1

HCID 68815111HCID 68815111, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Mix 5-iodo-N-methyl-N-propyl-isophthalamic acid methyl ester (220 mg, 0.61 mmol), 2-pyrrolidone (56 μL, 0.73 mmol), ethane-1,2-diamine (4 μL, 0.061 mmol), cesium carbonate (398 mg, 1.22) and copper (I) iodide (12 mg, 0.061 mmol) in 1,4-dioxane (4 mL). Heat the mixture to 110° C. for 1 h then stir at room temperature overnight. Dilute with dichloromethane and filter through a filtering agent. Concentrate and purify (silica gel chromatography, eluting with ethyl acetate and hexanes) to give the title compound (100 mg, 52%).

Workup

  1. filtrationfilter through a filtering agent
  2. concentrationConcentrate
  3. custompurify
  4. wash(silica gel chromatography, eluting with ethyl acetate and hexanes)

Sources & evidence

ORD record
ord-3ba360fcce0c4852a612c99fa6afdbbc
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

Loading…