Acetic Acid → HCID 22272615, compound

HRID 1064860Notes

Reaction equation

HRID 1064860 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH2:6])([CH3:3])[CH3:2].C1N2CN3CN(C2)CN1C3.[C:24](O)(=[O:26])C>O>[NH2:6][C:5]1[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:10][C:9]([CH:24]=[O:26])=[CH:8][C:7]=1[CH:11]([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 32484Diisopropylaniline

Product 1

HCID 22272615HCID 22272615, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
120 °C

Procedure

To a solution of 2,6-diisopropylaniline (10.0 g, 56.4 mmol) in acetic acid (160 ml) were added water (40 ml) and hexamethylenetetramine (15.8 g, 0.113 mol) and stirred at 120° C. for 3 hours. The reaction solution was diluted with water and extracted with chloroform. The organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (silica gel 200 g, developing solvent; hexane:ethyl acetate=10:1) to provide 10.6 g (yield 92%) of 4-amino-3,5-diisopropylbenzaldehyde as yellow solid.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by a silica gel column chromatography (silica gel 200 g, developing solvent; hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-d60249f484434bfa9d61828a01204bdf
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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