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

HRID 597891노트

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HRID 597891 반응식
[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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-905acc1a7caa433887df8d2fd7f9c358
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897601B2

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