Triethylamine → 2,5-dibromo-N'-[4-(octyloxy)benzoyl]benzohydrazide

HRID 458489

Reaktionsgleichung

Reaktionsgleichung von HRID 458489
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH2:12]([O:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([NH:27][NH2:28])=[O:26])=[CH:23][CH:22]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([NH:28][NH:27][C:25](=[O:26])[C:24]1[CH:29]=[CH:30][C:21]([O:20][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:22][CH:23]=1)=[O:5]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 42815334-Octoxybenzoyl hydrazineHCID 134505242,5-Dibromobenzoyl chloride

Produkt 1

HCID 219821022,5-dibromo-N'-[4-(octyloxy)benzoyl]benzohydrazideAusbeute 126,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Under a blanket of nitrogen, 2,5-dibromobenzoyl chloride (57.43 g, 0.11925 mol) was added to a solution of 4-octyloxybenzoic acid hydrazide (50.88 g, 0.1925 mol) and triethylamine (27 mL, 19.48 g, 0.1925 mol) in 800 mL of methylene chloride. The reaction mixture was stirred for 5 hours at room temperature. The precipitated solid was filtered off and re-crystallized from hot DMF/water gave 79.38 g (78% yield) 2,5-dibromo-N′-[4-(octyloxy)benzoyl]benzohydrazide.

Aufarbeitung

  1. filtrationThe precipitated solid was filtered off
  2. customre-crystallized from hot DMF/water

Quellen und Nachweise

ORD-Eintrag
ord-3c90c261d377472f80df95c24aa86fa6
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192657B2

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