Hydrochloric Acid → N-(4-diethylamino-2-butynyl)benzoylformamide

HRID 1087592Notes

Reaction equation

HRID 1087592 reaction equation
[CH2:1]([N:4]([C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:5]=[O:6])[C:2]#[CH:3].[CH2:15]=O.[CH2:17]([NH:19][CH2:20][CH3:21])[CH3:18].Cl>O1CCOCC1>[CH2:17]([N:19]([CH2:20][CH3:21])[CH2:15][C:3]#[C:2][CH2:1][N:4]([C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:5]=[O:6])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8021DiethylamineHCID 57042304N-(2-propynyl)benzoylformamide

Product 1

HCID 57072120N-(4-diethylamino-2-butynyl)benzoylformamideYield 74.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

N-(2-propynyl)benzoylformamide (0.36 g), 80% paraformaldehyde (90 mg) and diethylamine (162 mg) were added to anhydrous dioxane, 4 mg cuprous chloride was further added, and the mixture was heated at 70 to 80° C. for 1.5 hours with stirring. After cooling to room temperature, the reaction mixture was acidified with 5% hydrochloric acid. The separated aqueous layer was collected and washed with diethyl ether, 5% aqueous solution of caustic soda was added under ice cooling to make the solution weakly alkaline, and the alkaline solution was extracted with diethyl ether. The etheral extract was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The oily residue thus obtained was purified by silica gel column chromatography (Wako Gel C-200; chloroform), giving 0.39 g of the objective compound.

Workup

  1. additionwas further added
  2. temperatureAfter cooling to room temperature
  3. customThe separated aqueous layer was collected
  4. washwashed with diethyl ether, 5% aqueous solution of caustic soda
  5. additionwas added under ice cooling
  6. extractionthe alkaline solution was extracted with diethyl ether
  7. extractionThe etheral extract
  8. washwas washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe oily residue thus obtained
  12. customwas purified by silica gel column chromatography (Wako Gel C-200; chloroform)

Sources & evidence

ORD record
ord-b21ce78671fa44d19cbf383ef690d021
Source dataset
uspto-grants-1991_07
Patent number
US05036098

Reaction notes

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