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

HRID 597891ノート

反応式

HRID 597891 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-905acc1a7caa433887df8d2fd7f9c358
出典データセット
uspto-grants-2011_03
特許番号
US07897601B2

反応ノート

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