Dimethylformamide dimethyl acetal → HCID 54332284, compound

HRID 1906168Notes

Reaction equation

HRID 1906168 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[CH:9]=[CH:10][C:11](=[O:15])[NH:12][C:13]=1[CH3:14])=[O:7].CO[CH:18](OC)[N:19]([CH3:21])[CH3:20]>O1CCOCC1>[CH3:18][N:19]([CH3:21])[CH:20]=[CH:14][C:13]1[NH:12][C:11](=[O:15])[CH:10]=[CH:9][C:8]=1[C:6]([C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)=[O:7]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 13560736HCID 13560736, compound

Product 1

HCID 54332284HCID 54332284, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

C-1. 6-[2-(Dimethylamino)ethenyl]-5-(2-furanylcarbonyl)-2(1H)-pyridinone--A mixture containing 30.5 g of 5-(2-furanylcarbonyl)-6-methyl-2(1H)-pyridinone, 400 ml of p-dioxane and 25 ml of dimethylformamide dimethyl acetal was heated under reflux for 6 hours and then allowed to cool. The separated crystalline product was collected, washed with isopropyl alcohol and dried in a vacuum oven at 80°-85° C. to yield 28.4 g of 6-[2-(dimethylamino)ethenyl]-5-(2-furanylcarbonyl)-2(1H)-pyridinone, m.p. 238°-240° C. with decomposition. The mother liquor on concentration yielded another 5.6 g of product.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. temperatureto cool
  4. customThe separated crystalline product was collected
  5. washwashed with isopropyl alcohol
  6. customdried in a vacuum oven at 80°-85° C.

Sources & evidence

ORD record
ord-5a3c6b8d028d4a7083d3808efb99eb44
Source dataset
uspto-grants-1987_03
Patent number
US04650806

Reaction notes

Loading…