Water → HCID 12968695, compound

HRID 1656392Notes

Reaction equation

HRID 1656392 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])=O.[C:16]([CH2:18][C:19]([NH2:21])=[O:20])#[N:17].C[O-].[Na+].O>CN(C)C=O.C(O)(=O)C>[C:16]([C:18]1[C:19](=[O:20])[NH:21][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[O:13][CH3:14])=[CH:4][CH:3]=1)#[N:17]

Participants

7

Reactant 4

HCID 962WaterHCID 7898CyanoacetamideHCID 10942334Sodium MethoxideHCID 54435623HCID 54435623, compound

Product 1

HCID 12968695HCID 12968695, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 3-dimethylamino-1-(2-methoxyphenyl)-2-propene-1-one (5.74 g), cyanoacetamide (2.48 g) and sodium methoxide (from sodium hydride (50%, 4.32 g) and methanol (3.5 ml)) in dry dimethylformamide was heated under reflux for 10 hours. The reaction mixture was poured into water, acidified to pH4 with glacial acetic acid and extracted with ethyl acetate. The ethyl acetate extract was evaporated under reduced pressure to low volume and water was added to cause precipitation of a crude product (3.67 g) which was collected and recrystallised twice from dimethylformamide to yield the title compound, 1.68 g, m.p. 236°-238° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 hours
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. customwas evaporated under reduced pressure to low volume and water
  6. additionwas added
  7. customprecipitation of a crude product (3.67 g) which
  8. customwas collected
  9. customrecrystallised twice from dimethylformamide

Sources & evidence

ORD record
ord-52327bd6952c4a26aaaff0788a12c40a
Source dataset
uspto-grants-1993_10
Patent number
US05254571

Reaction notes

Loading…