Water → 2,6-dimethyl-N-allenyl-N-(2-furoyl)-aniline

HRID 851482Notes

Reaction equation

HRID 851482 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:3]=1[N:4]([C:8]([C:10]1[O:11][CH:12]=[CH:13][CH:14]=1)=[O:9])[CH2:5][C:6]#[CH:7].O>O1CCCC1>[CH3:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:3]=1[N:4]([CH:5]=[C:6]=[CH2:7])[C:8]([C:10]1[O:11][CH:12]=[CH:13][CH:14]=1)=[O:9]

Participants

4

Reactant 2

HCID 962WaterHCID 131504722,6-dimethyl-N-(2-furoyl)-N-propargyl-aniline

Product 1

HCID 204797872,6-dimethyl-N-allenyl-N-(2-furoyl)-anilineYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

50 g (0.2 mol) of 2,6-dimethyl-N-(2-furoyl)-N-propargyl-aniline were dissolved in 200 ml of anhydrous tetrahydrofuran, and 150 mg of potassium tert.-butylate were added. During this procedure, the temperature of the solution rose to about 50° C., the solution becoming colored. The reaction mixture was left to stand for 2 hours and then poured onto 500 ml of water. The crystalline product which had precipitated was filtered off, dried and recrystallized from ethyl acetate/petroleum ether. 24 g (48% of theory) of 2,6-dimethyl-N-allenyl-N-(2-furoyl)-aniline of melting point 138°-41° C. were obtained. (The 1H-NMR spectrum indicated complete isomerization.) ##STR100##

Workup

  1. customrose to about 50° C.
  2. waitThe reaction mixture was left
  3. customThe crystalline product which had precipitated
  4. filtrationwas filtered off
  5. customdried
  6. customrecrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-e4cf72f3fe184f9482b0a82379d19671
Source dataset
uspto-grants-1983_05
Patent number
US04385069

Reaction notes

Loading…