2,6-Dimethylaniline → HCID 12877376, compound

HRID 1065023Notes

Reaction equation

HRID 1065023 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:17][C:18]1[N:23]=[CH:22][CH:21]=[CH:20][N:19]=1>CN(C)C=O.[I-].[K+]>[N:19]1[CH:20]=[CH:21][CH:22]=[N:23][C:18]=1[CH2:17][NH:4][C:3]1[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:2]=1[CH3:1]

Participants

6

Reactant 3

HCID 68962,6-DimethylanilineHCID 11430Potassium CarbonateHCID 128773712-(Chloromethyl)pyrimidine

Product 1

HCID 12877376HCID 12877376, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

48.4 g (0.4 mol) of 2,6-dimethylaniline, 55.3 g (0.4 mol) of potassium carbonate and 0.2 g of potassium iodide were heated to 100° C. in 60 ml of dimethylformamide, and 25.7 g (0.2 mol) of 2-chloromethyl-pyrimidine were then added dropwise. The reaction mixture was subsequently stirred at 100° C. for 5 hours and then poured onto 500 g of ice. It was then extracted three times with 150 ml of methylene chloride each time. The combined organic phases were dried over sodium sulphate and concentrated in vacuo. The residue was distilled under a high vacuum. 30 g (70% of theory) of N-(pyrimidin-2-yl-methyl)-2,6-dimethylaniline were obtained as a colorless oil of boiling point 150° C./0.2 mm Hg. ##STR13##

Workup

  1. extractionIt was then extracted three times with 150 ml of methylene chloride each time
  2. dry with materialThe combined organic phases were dried over sodium sulphate
  3. concentrationconcentrated in vacuo
  4. distillationThe residue was distilled under a high vacuum

Sources & evidence

ORD record
ord-e8e9104a901f41069e118af771b11c6f
Source dataset
uspto-grants-1982_05
Patent number
US04328029

Reaction notes

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