Triethylamine → 5-(2,4-Dichlorophenyl)-4-methylpenta-2,4-dienoic acid [3-(4-chlorophenyl)allyl]amide

HRID 597891Notes

Reaction equation

HRID 597891 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]=[C:10]([CH3:16])[CH:11]=[CH:12][C:13]([OH:15])=O.C(Cl)(=O)C(Cl)=O.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]=[CH:31][CH2:32][NH2:33])=[CH:26][CH:25]=1.CCN(CC)CC>C(Cl)Cl.CN(C=O)C.C1COCC1.CCOC(C)=O>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([CH:30]=[CH:31][CH2:32][NH:33][C:13](=[O:15])[CH:12]=[CH:11][C:10]([CH3:16])=[CH:9][C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])=[CH:28][CH:29]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 536960003-(4-Chlorophenyl)allylamineHCID 724731095-(2,4-Dichlorophenyl)-4-methylpenta-2,4-dienoic acid

Product 1

HCID 724731225-(2,4-Dichlorophenyl)-4-methylpenta-2,4-dienoic acid [3-(4-chlorophenyl)allyl]amideYield 78.8%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

5-(2,4-Dichlorophenyl)-4-methylpenta-2,4-dienoic acid (1 g, 0.0039 mol) was suspended in CH2Cl2 (10 mL). Oxalyl chloride (0.5 mL, 1.5 eq) was added, followed by 1 drop of DMF. After 2 hours the volatiles were removed, the residue taken up in THF (10 mL), and the mixture cooled to 0° C. A mixture of 3-(4-chlorophenyl)allylamine (0.7 g, 1.1 eq, 0.0042 mol, prepared as shown in Scheme 4) and Et3N (0.82 mL, 0.0042 mol, 1.5 eq) in THF (5 mL) was added dropwise. After 1 hour, TLC analysis showed complete conversion of the starting materials and the mixture was then diluted with EtOAc. The organic layer washed with NH4Cl(sat), dried (MgSO4), and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (0-10-20-30-40% EtOAc in hexanes) to give 1.25 g of 5-(2,4-dichlorophenyl)-4-methylpenta-2,4-dienoic acid [3-(4-chlorophenyl)allyl]amide.

Workup

  1. customAfter 2 hours the volatiles were removed
  2. additionwas added dropwise
  3. washThe organic layer washed with NH4Cl(sat)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (0-10-20-30-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-905acc1a7caa433887df8d2fd7f9c358
Source dataset
uspto-grants-2011_03
Patent number
US07897601B2

Reaction notes

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