Sodium Iodide → N-(2,2-Diethoxyethyl)-2,3-dimethylbenzenamine

HRID 342629Notes

Reaction equation

HRID 342629 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20]Br)[CH3:17].[I-].[Na+]>CN(C=O)C.CCOC(C)=O>[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20][NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[C:8]([CH3:9])[C:2]=1[CH3:1])[CH3:17]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 68932,3-DimethylanilineHCID 10796Cesium carbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 70207399N-(2,2-Diethoxyethyl)-2,3-dimethylbenzenamine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2,3-dimethylaniline (2.0 mL, 16.6 mmol) in 30 mL of dry DMF at room temperature was added cesium carbonate (5.4 g, 17 mmol), then bromoacetaldehyde diethylacetal (2.50 mL, 16.6 mmol). The solution was warmed to 110° C., and stirred for four days. Sodium iodide (100 mg, 0.6 mmol) was added, and the reaction stirred for an additional 24 hours. The reaction mixture was poured into EtOAc, washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the titled product as a brown oil which was used directly in the next step without further purification.

Workup

  1. stirringthe reaction stirred for an additional 24 hours
  2. washwashed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2ad23d60cf3346f8a235069eeca0d5b4
Source dataset
uspto-grants-1999_01
Patent number
US05859012

Reaction notes

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