Dibromomethane → Rdea806

HRID 425305

Reaktionsgleichung

Reaktionsgleichung von HRID 425305
ClC(Cl)C(O)=O.N[C:8]1[N:9]([C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]([CH:38]3[CH2:40][CH2:39]3)=[CH:30][CH:29]=2)[C:10]([S:13][CH2:14][C:15]([NH:17][C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][C:19]=2[Cl:27])=[O:16])=[N:11][N:12]=1.N([O-])=O.[Na+].[Br:45]CBr>[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Br:45][C:8]1[N:9]([C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]([CH:38]3[CH2:40][CH2:39]3)=[CH:30][CH:29]=2)[C:10]([S:13][CH2:14][C:15]([NH:17][C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][C:19]=2[Cl:27])=[O:16])=[N:11][N:12]=1

Komponenten

6

Edukt 4

HCID 3024DibromomethaneHCID 6597Dichloroacetic AcidHCID 23668193Sodium NitriteHCID 573589664-[[2-[[5-amino-4-(4-cyclopropyl-1-naphthalenyl)-4H-1,2,4-triazol-3-yl]thio]acetyl]amino]-3-chloroBenzoic acid

Produkt 1

HCID 16221816Rdea806Ausbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 165294Benzyltriethylammonium bromideKatalysator

Versuchsvorschrift

Dichloroacetic acid (0.35 mL, 4.2 mmol) was added to a mixture of compound 6 (1.04 g, 2.1 mmol), benzyltriethyl ammonium bromide (1.65 g, 6.1 mmol) and sodium nitrite (2.9 g, 42.1 mmol) in dibromomethane (44 mL). The mixture was stirred at room temperature for 18 hours in the dark. The reaction mixture was then concentrated tad the resulting residue was purified by column chromatography (95% dichloromethane/5% methanol) to afford 393 mg 34% yield of 4-(2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetamido)-3-chlorobenzoic acid (7).

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated tad the resulting residue
  2. customwas purified by column chromatography (95% dichloromethane/5% methanol)

Quellen und Nachweise

ORD-Eintrag
ord-70b84c8b7096400980c225f134dea2b7
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106205B2

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