Sodium Azide → Methyl 6-azido-4-(4-bromo-2-chlorophenylamino)-5-chloronicotinate

HRID 494700Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 494700
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][O:6][C:7](=[O:25])[C:8]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[Cl:22])=[C:12]([Cl:23])[C:11](Cl)=[N:10][CH:9]=1>CN(C=O)C.O>[CH3:5][O:6][C:7](=[O:25])[C:8]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[Cl:22])=[C:12]([Cl:23])[C:11]([N:1]=[N+:2]=[N-:3])=[N:10][CH:9]=1

Komponenten

5

Edukt 2

HCID 33557Sodium AzideHCID 11603943Methyl 4-(4-bromo-2-chlorophenylamino)-5,6-dichloronicotinate

Produkt 1

HCID 59519382Methyl 6-azido-4-(4-bromo-2-chlorophenylamino)-5-chloronicotinate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium azide (4.4 g, 68 mmol) was added to a suspension of 4-(4-bromo-2-chlorophenylamino)-5,6-dichloronicotinic acid methyl ester (26) (13.89 g, 33.8 mmol) in DMF (200 mL) and the mixture allowed to stir at room temperature overnight. The solution was diluted with water (600 mL) and the resulting white precipitate was collected by filtration and washed with water. The solids were dissolved into THF. Two volumes of diethyl ether were added and the organic solution washed with brine, dried over NaSO4, filtered, and concentrated in vacuo to the desired product (27) as a light yellow solid (12.94 g, 92%).

Aufarbeitung

  1. filtrationthe resulting white precipitate was collected by filtration
  2. washwashed with water
  3. dissolutionThe solids were dissolved into THF
  4. additionTwo volumes of diethyl ether were added
  5. washthe organic solution washed with brine
  6. dry with materialdried over NaSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to the desired product (27) as a light yellow solid (12.94 g, 92%)

Quellen und Nachweise

ORD-Eintrag
ord-85f60a9474a742ee938e2975590010d8
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538120B2

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