2,6-Dimethylaniline → N-(1,3-dioxolan-5-ylmethyl)-2,6-dimethylaniline

HRID 268050

Reaction equation

HRID 268050 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].Cl[CH2:11][CH:12]1[O:16][CH2:15][O:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CC)(CC)CC)C>[O:16]1[CH:12]([CH2:11][NH:4][C:3]2[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:2]=2[CH3:1])[CH2:13][O:14][CH2:15]1

Participants

5

Reactant 3

HCID 68962,6-DimethylanilineHCID 11430Potassium CarbonateHCID 2401534-(Chloromethyl)-1,3-dioxolane

Product 1

HCID 21447788N-(1,3-dioxolan-5-ylmethyl)-2,6-dimethylaniline

Reagents, catalysts & solvents 1

HCID 5946Tetraethylammonium ChlorideCatalyst

Procedure

2,6-Dimethylaniline (94.5 grams), 5-chloromethyl-1,3-dioxolane (31.8 grams), potassium carbonate (36.7 grams) and tetraethylammonium chloride (2 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at reflux for a period of 48 hours. After this time the mixture was filtered and distilled to yield the desired product N-(1,3-dioxolan-5-ylmethyl)-2,6-dimethylaniline having a boiling point of 132°C under aspirator pressure.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for a period of 48 hours
  5. filtrationAfter this time the mixture was filtered
  6. distillationdistilled

Sources & evidence

ORD record
ord-41eda4bb2c954e3691eb720b45327371
Source dataset
uspto-grants-1976_03
Patent number
US03946045

Linked notes

Loading…