2,6-Diethylaniline → HCID 15680271, compound

HRID 483449Notes

Reaction equation

HRID 483449 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:4]=1[NH2:5])[CH3:2].[C:12](Cl)(=[O:15])[CH:13]=[CH2:14]>C(OCC)(=O)C>[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:4]=1[NH:5][C:12](=[O:15])[CH:13]=[CH2:14])[CH3:2]

Participants

4

Reactant 2

HCID 113692,6-DiethylanilineHCID 13140Acryloyl chloride

Product 1

HCID 15680271HCID 15680271, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a cold solution of 2.6-diethylaniline (60.6 g, 0.07 mole) in ethyl acetate (600 ml) was added a solution of acryloyl chloride (45.2 g, 0.5 mole) in ethyl acetate (50 ml) over a 30 minute period. The ice bath was removed and the solution stirred for 4 hours. 10 Percher hydrochloric acid was added and the solution stirred gently for 15 minutes. The layers were separated and the organic layer washed with water, dried over sodium sulfate, filtered and the solvents removed on a rotary evaporator leaving an orange solid. The solid was recrystallized from ethyl acetate/hexane and the product filtered and dried.

Workup

  1. customThe ice bath was removed
  2. addition10 Percher hydrochloric acid was added
  3. stirringthe solution stirred gently for 15 minutes
  4. customThe layers were separated
  5. washthe organic layer washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvents removed on a rotary evaporator
  9. customleaving an orange solid
  10. customThe solid was recrystallized from ethyl acetate/hexane
  11. filtrationthe product filtered
  12. customdried

Sources & evidence

ORD record
ord-64b72341b43945e6b0f68f80a6675146
Source dataset
uspto-grants-1993_07
Patent number
US05225444

Reaction notes

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