Triethylamine → 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(5-bromo-2-furancarboxamido)propyloxy)-benzene

HRID 377708

Reaktionsgleichung

Reaktionsgleichung von HRID 377708
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([Cl:12])=[CH:10][C:9]([O:13][CH2:14][CH:15]=[C:16]([Cl:18])[Cl:17])=[CH:8][C:7]=1[Cl:19].[Br:20][C:21]1[O:25][C:24]([C:26](O)=[O:27])=[CH:23][CH:22]=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl>C(OCC)(=O)C.C(Cl)(Cl)Cl>[Cl:19][C:7]1[CH:8]=[C:9]([O:13][CH2:14][CH:15]=[C:16]([Cl:18])[Cl:17])[CH:10]=[C:11]([Cl:12])[C:6]=1[O:5][CH2:4][CH2:3][CH2:2][NH:1][C:26]([C:24]1[O:25][C:21]([Br:20])=[CH:22][CH:23]=1)=[O:27]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 685115-Bromo-2-furanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 158697443-[2,6-Dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propylamine

Produkt 1

HCID 220067713,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(5-bromo-2-furancarboxamido)propyloxy)-benzeneAusbeute 67,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 0.35 g of 4-(3-aminopropyloxy)-3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)benzene, 0.19 g of 5-bromo-2-furancarboxylic acid, 0.18 ml of triethylamine and 10 ml of chloroform was added 0.23 g of WSC hydrochloride, while stirring at room temperature. After stirring at room temperature for 6 hours, the reaction mixture was concentrated to give a residue. The residue was dissolved in 50 ml of ethyl acetate, and the ethyl acetate layer was successively washed with 10% hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated to give a residue. The residue was subjected to silica gel chromatography, which afforded 0.35 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(5-bromo-2 -furancarboxamido)propyloxy)benzene (64% yield), nD24.0 1.5918.

Aufarbeitung

  1. stirringAfter stirring at room temperature for 6 hours
  2. concentrationthe reaction mixture was concentrated
  3. customto give a residue
  4. washthe ethyl acetate layer was successively washed with 10% hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated saline solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto give a residue

Quellen und Nachweise

ORD-Eintrag
ord-90fd8e9d3e7d48c5bc03484c0e6da5bf
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06028100

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