3,4-Dichlorobenzaldehyde → (E)-N-[[N-[2-[3-(3,4-dichlorophenyl)acryloyl]phenyl]-N-methylcarbamoyl]methyl]pivalamide

HRID 48345Notes

Reaction equation

HRID 48345 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]([CH3:21])[C:11]([CH2:13][NH:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])=[O:12])(=[O:3])[CH3:2].[Cl:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH:26]=O>[OH-].[Na+].CO>[Cl:22][C:23]1[CH:24]=[C:25](/[CH:26]=[CH:2]/[C:1]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:10]([CH3:21])[C:11]([CH2:13][NH:14][C:15](=[O:20])[C:16]([CH3:17])([CH3:19])[CH3:18])=[O:12])=[O:3])[CH:28]=[CH:29][C:30]=1[Cl:31]

Participants

5

Reactant 2

HCID 227103,4-DichlorobenzaldehydeHCID 22742393N-[[N-(2-acetylphenyl)-N-methylcarbamoyl]methyl]pivalamide

Product 1

HCID 22742421(E)-N-[[N-[2-[3-(3,4-dichlorophenyl)acryloyl]phenyl]-N-methylcarbamoyl]methyl]pivalamideYield 27.9%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 887MethanolSolvent

Procedure

5 drops of 3M sodium hydroxide solution were added to a mixture of 160 mg (0.52 mmol) of N-[[N-(2-acetylphenyl)-N-methylcarbamoyl]methyl]pivalamide and 100 mg (0.57 mmol) of 3,4-dichlorobenzaldehyde in 3 ml of methanol. After 1 hr at room temperature the solvent was removed by evaporation and the residue chromatographed on silica gel using ethyl acetate/petrol (55:45) for the elution. There was obtained 65 mg of (E)-N-[[N-[2-[3-(3,4-dichlorophenyl)acryloyl]phenyl]-N-methylcarbamoyl]methyl]pivalamide as a yellow gum. MS: m/e 463 [M+H]+.

Workup

  1. customAfter 1 hr at room temperature the solvent was removed by evaporation
  2. customthe residue chromatographed on silica gel
  3. washfor the elution

Sources & evidence

ORD record
ord-de84e0107631419c9b5a66ac0f924e37
Source dataset
uspto-grants-2004_03
Patent number
US06703387B2

Reaction notes

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