2,3-Diaminotoluene → HCID 178467355, compound

HRID 885426Notes

Reaction equation

HRID 885426 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].[CH2:10]([O:12][C:13](OCC)(OCC)OCC)[CH3:11]>C(OCC)(=O)C>[CH2:10]([O:12][C:13]1[NH:1][C:2]2[C:3]([CH3:9])=[CH:4][CH:5]=[CH:6][C:7]=2[N:8]=1)[CH3:11]

Participants

4

Reactant 2

HCID 175932,3-DiaminotolueneHCID 66213Tetraethyl orthocarbonate

Product 1

HCID 178467355HCID 178467355, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

2,3-Diaminotoluene (6.09 g, 49.8 mmol) and tetraethoxymethane (25 mL, 119 mmol) were mixed, and the mixture was stirred at 130° C. for 16 hr. The mixture was cooled to room temperature, diluted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30) to give the title compound (6.89 g, 78%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30)

Sources & evidence

ORD record
ord-52e162d3dbb344d8a4b8be5ad45ff782
Source dataset
uspto-grants-2012_08
Patent number
US08242151B2

Reaction notes

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