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Azobisisobutyronitrile → 2-(4-bromomethylphenyl)-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide

HRID 1107482
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1107482
[Br:1]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.[CH2:21]([O:25][C:26]([N:28]([C:45]1[C:50]([O:51][CH3:52])=[N:49][C:48]([CH3:53])=[CH:47][N:46]=1)[S:29]([C:32]1[C:33]([C:38]2[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=2)=[N:34][CH:35]=[CH:36][CH:37]=1)(=[O:31])=[O:30])=[O:27])[CH:22]([CH3:24])[CH3:23]>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:44][C:41]1[CH:42]=[CH:43][C:38]([C:33]2[C:32]([S:29]([N:28]([C:26]([O:25][CH2:21][CH:22]([CH3:23])[CH3:24])=[O:27])[C:45]3[C:50]([O:51][CH3:52])=[N:49][C:48]([CH3:53])=[CH:47][N:46]=3)(=[O:31])=[O:30])=[CH:37][CH:36]=[CH:35][N:34]=2)=[CH:39][CH:40]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 21186261HCID 21186261, Verbindung

Produkt 1

HCID 211862832-(4-bromomethylphenyl)-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamideAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943
Carbon Tetrachloride
Lösungsmittel

Versuchsvorschrift

N-Bromosuccinimide (2.99 g) and azobisisobutyronitrile (275 mg) were added to a solution of N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)-2-(4-methylphenyl)pyridine-3-sulphonamide (7.9 g) in carbon tetrachloride (150 ml) and the mixture was heated under reflux for 4 hours. Insoluble material was removed by filtration and the fitrate was concentrated by evaporation. The residue was redissolved in ethyl acetate (200 ml) and the solution was washed with water (100 ml) and saturated sodium chloride solution (100 ml). The solution was dried (MgSO4) and the solvent was removed by evaporation. The residue was triturated with ethyl acetate/hexane (3:7 v/v, 80 ml) to give 2-(4-bromomethylphenyl)-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)-pyridine-3-sulphonamide (6.5 g), m.p. 125-128° C.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customInsoluble material was removed by filtration
  4. concentrationthe fitrate was concentrated by evaporation
  5. dissolutionThe residue was redissolved in ethyl acetate (200 ml)
  6. washthe solution was washed with water (100 ml) and saturated sodium chloride solution (100 ml)
  7. dry with materialThe solution was dried (MgSO4)
  8. customthe solvent was removed by evaporation
  9. customThe residue was triturated with ethyl acetate/hexane (3:7 v/v, 80 ml)

Quellen und Nachweise

ORD-Eintrag
ord-5a9a03a2e34840a884aad1d10c587a3d
Quelldatensatz
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06060475

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