Hydrochloric Acid → HCID 86077028, compound

HRID 734806Notes

Reaction equation

HRID 734806 reaction equation
[Na+].[I-:2].CN(C)CCN.Br[C:10]1[CH:11]=[CH:12][C:13]([O:18][CH2:19][CH2:20][OH:21])=[C:14]([CH:17]=1)[CH:15]=[O:16].CNCCNC.Cl>O1CCOCC1.[Cu]I>[OH:21][CH2:20][CH2:19][O:18][C:13]1[CH:12]=[CH:11][C:10]([I:2])=[CH:17][C:14]=1[CH:15]=[O:16]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 66053N,N-DimethylethylenediamineHCID 14688771HCID 14688771, compound

Product 1

HCID 86077028HCID 86077028, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

Under an argon atmosphere 0.91 g (4.80 mmol) of CuI, 14.37 g (95.89 mmol) of NaI, and 6.13 mL (57.53 mmol) of N,N-dimethylethane-1,2-diamine were added to a solution of 11.75 g (47.945 mmol) of 5-bromo-2-(2-hydroxyethoxy)benzaldehyde in 50 mL of 1,4-dioxane and the mixture was stirred for 16 hours at 110° C. Another 6.13 mL (57.53 mmol) of N,N′-dimethylethane-1,2-diamine was added and the mixture was stirred for 8 hours at 110° C. The reaction mixture was cooled to RT, acidified with 12% aqueous HCl, and stirred for 30 minutes. The aqueous phase was exhaustively extracted with EtOAc, and the organic phase was washed with dilute aqueous ammonia solution and water, dried over magnesium sulfate, and evaporated down in vacuo. Yield: 9.78 g (52% of theoretical); C9H9IO3 (M=292.070); calc.: molpeak (M+H)+: 292; found: molpeak (M+H)+: 292.

Workup

  1. stirringthe mixture was stirred for 8 hours at 110° C
  2. temperatureThe reaction mixture was cooled to RT
  3. stirringstirred for 30 minutes
  4. extractionThe aqueous phase was exhaustively extracted with EtOAc
  5. washthe organic phase was washed with dilute aqueous ammonia solution and water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated down in vacuo

Sources & evidence

ORD record
ord-e2eb553a35cb49f4af3b4eab33fbd010
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

Loading…