2,6-Dimethylaniline → HCID 21419811, compound

HRID 268044Notes

Reaction equation

HRID 268044 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:17][CH2:16][CH2:15][CH2:14][O:13]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:13]1[CH2:14][CH2:15][CH2:16][O:17][CH:12]1[CH2:11][NH:4][C:3]1[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 68962,6-DimethylanilineHCID 11430Potassium CarbonateHCID 5599722-(Chloromethyl)-1,3-dioxane

Product 1

HCID 21419811HCID 21419811, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,6-Dimethylaniline (75 grams), 2-chloromethyl-1,3-dioxane prepared in Example 1 (35 grams), potassium carbonate (30 grams) and dimethyl formamide (50 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was then heated at reflux for a period of about 16 hours. After this time the reaction mixture was filtered and the filtrate was distilled to yield the desired product N-(1,3-dioxan-2-ylmethyl)-2,6-dimethylaniline as a residue which crystallized upon standing at room temperature.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureThe reaction mixture was then heated
  4. temperatureat reflux for a period of about 16 hours
  5. filtrationAfter this time the reaction mixture was filtered
  6. distillationthe filtrate was distilled

Sources & evidence

ORD record
ord-cc3d865605c740528f0c58d0a203b606
Source dataset
uspto-grants-1976_03
Patent number
US03946043

Reaction notes

Loading…