Formaldehyde → HCID 21829921, compound

HRID 1600546Notes

Reaction equation

HRID 1600546 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[NH:9][C:10](=[O:27])[C:11]([NH:14][C:15](=[O:26])[CH:16]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH:17][CH2:18][CH3:19])([CH3:13])[CH3:12].[C:28](=O)([O-])[O-].[K+].[K+].C=O.O>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[NH:9][C:10](=[O:27])[C:11]([N:14]1[C:15](=[O:26])[CH:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:17]([CH2:18][CH3:19])[CH2:28]1)([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 22375581HCID 22375581, compound

Product 1

HCID 21829921HCID 21829921, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-(2,5-dichlorophenyl)-2-(α-ethylaminophenylacetylamino)isobutyramide (0.9 g) in ethanol (15 mL) were added potassium carbonate (0.5 g) and paraformaldehyde (0.5 g), and the mixture was heated at reflux for 4 hours. After the reaction solution was added to water, the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the resulting crude product was purified by thin-layer chromatography (silica gel, diethyl ether/n-hexane=1/1) to give 0.4 g of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationAfter distilling off the solvent under reduced pressure
  7. customthe resulting crude product was purified by thin-layer chromatography (silica gel, diethyl ether/n-hexane=1/1)

Sources & evidence

ORD record
ord-767cf071e4e847d19f9df04a3ebf3b54
Source dataset
uspto-grants-1999_11
Patent number
US05977027

Reaction notes

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