2,6-Dimethylaniline → 1,3-Dioxolane-2-methanamine, N-(2,6-dimethylphenyl)-

HRID 1605038Notes

Reaction equation

HRID 1605038 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][CH2:14][O:13]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:13]1[CH2:14][CH2:15][O:16][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 757272-(Chloromethyl)-1,3-dioxolane

Product 1

HCID 1047101,3-Dioxolane-2-methanamine, N-(2,6-dimethylphenyl)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,6-Dimethylaniline (75 grams), 2-chloromethyl- 1,3-dioxolane (25 grams), potassium carbonate (35 grams) and dimethylformamide (50 ml) 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 about 18 hours. After this time the mixture was filtered and distilled to yield the desired product N-(1,3-dioxolan-2-ylmethyl-2,6-dimethylaniline.

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 about 18 hours
  5. filtrationAfter this time the mixture was filtered
  6. distillationdistilled

Sources & evidence

ORD record
ord-e23ed0fbb53244e2ab38625eddeea61e
Source dataset
uspto-grants-1976_04
Patent number
US03948950

Reaction notes

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