2,4,6-Trimethylaniline → HCID 24881570, compound

HRID 2369378Notes

Reaction equation

HRID 2369378 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].[CH:10](OCC)(OCC)OCC.[CH3:20][C:21]1[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[C:22]=1[NH2:23]>C(O)(=O)C>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH:4][CH:10]=[N:23][C:22]1[C:24]([CH3:29])=[CH:25][C:26]([CH3:28])=[CH:27][C:21]=1[CH3:20]

Participants

5

Reactant 3

HCID 69132,4,6-TrimethylanilineHCID 31214Ethyl orthoformateHCID 796472,6-Difluoroaniline

Product 1

HCID 24881570HCID 24881570, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Conditions

Temperature
120 °C

Procedure

Acetic acid (0.086 mL, 1.5 mmol) was added to a round bottom flask charged with 2,6-difluoroaniline (3 mL, 30 mmol) and triethyl orthoformate (5 mL, 30 mmol). A vigreux column was attached and the solution was heated with stirring to 120° C. for 2 hours. 2,4,6-trimethylaniline (4.22 mL, 30 mmol) was then added to the reaction mixture. The solution was heated to reflux for an additional 2 hours and cooled to room temperature, whereupon crude product precipitated. Trituration with cold hexanes and vacuum filtration provided pure N-(2,6-difluorophenyl)-N′(mesityl)-formamidine (5.35 g, 65%) as a colorless powder.

Workup

  1. temperaturethe solution was heated
  2. temperatureThe solution was heated
  3. temperatureto reflux for an additional 2 hours
  4. temperaturecooled to room temperature, whereupon crude product
  5. customprecipitated
  6. filtrationTrituration with cold hexanes and vacuum filtration

Sources & evidence

ORD record
ord-c1f1648a07864b3fb66d107247121cc1
Source dataset
uspto-grants-2014_04
Patent number
US08703965B2

Reaction notes

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