Dimethylformamide → HCID 54435623, compound

HRID 1017697Notes

Reaction equation

HRID 1017697 reaction equation
CO[CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].CO[CH:14](OC)[N:15]([CH3:17])[CH3:16].CN(C)[CH:22]=[O:23]>C(OCC)(=O)C>[CH3:14][N:15]([CH3:17])[CH:16]=[CH:3][C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=1[O:23][CH3:22])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 776982-Methoxy-1-phenylethanoneHCID 78373Dimethylformamide dimethyl acetal2×

Product 1

HCID 54435623HCID 54435623, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stirred mixture of 2-methoxyacetophenone (5.5 ml) and dimethylformamide dimethylacetal (6.7 ml) in dry dimethylformamide (40 ml) was heated under reflux for 18 hours. A further quantity of dimethylformamide dimethylacetal (1 ml) was added and reflux continued for 3 hours. The cooled reaction mixture was diluted with ethyl acetate, washed with water and brine, dried (magnesium sulphate) and evaporated under reduced pressure yielding 3-dimethylamino-1-(2-methoxyphenyl)-2-propene-1-one as an orange oil. Further product remained in the aqueous extract which was evaporated under reduced pressure to yield a residue which was dissolved in ethyl acetate. The filtered solution was washed with water and brine, dried (magnesium sulphate) and evaporated under reduced pressure to yield a further quantity of orange oil. Total yield was 5.74 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. temperaturereflux
  4. customThe cooled reaction mixture
  5. washwashed with water and brine
  6. dry with materialdried (magnesium sulphate)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c9afbf23baa54faeaa6bc664361281d7
Source dataset
uspto-grants-2002_11
Patent number
US06479520B1

Reaction notes

Loading…