1,3-Dibromo-5,5-dimethylhydantoin → HCID 178461196, Verbindung

HRID 81098

Reaktionsgleichung

Reaktionsgleichung von HRID 81098
[Cl:1][C:2]1[C:7]2[N:8]([CH2:11][C@H:12]3[CH2:17][CH2:16][C@H:15]([CH3:18])[CH2:14][CH2:13]3)[CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([Cl:19])[N:3]=1.P([O-])([O-])(O)=O.[Na+].[Na+].[Br:27]N1C(C)(C)C(=O)N(Br)C1=O>C1COCC1.CCOC(C)=O>[Br:27][C:9]1[N:8]([CH2:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([CH3:18])[CH2:14][CH2:13]2)[C:7]2[C:2]([Cl:1])=[N:3][C:4]([Cl:19])=[CH:5][C:6]=2[N:10]=1

Komponenten

6

Edukt 3

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 24203Sodium Phosphate, DibasicHCID 178461251HCID 178461251, Verbindung

Produkt 1

HCID 178461196HCID 178461196, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

4,6-dichloro-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine (1 g, 3.35 mmol) was dissolved in THF (10 mL). Disodium hydrogen phosphate (1.43 g, 10.1 mmol) was added, and the reaction was warmed to 35° C. with stirring. 1,3-dibromo-5,5-dimethylhydantoin (1.15 g, 4.02 mmol) was added in 1 portion, and the reaction was continued with stirring at 35° C. After 45 minutes, the reaction was diluted with EtOAc (100 mL) and washed with aqueous NaHSO3 and brine. The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue on a silica gel column with 0 to 50% EtOAc/hexanes provided 2-bromo-4,6-dichloro-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine.

Aufarbeitung

  1. stirringwith stirring at 35° C
  2. washwashed with aqueous NaHSO3 and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the residue on a silica gel column with 0 to 50% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-0c27f33962f648758fd76403fb149c44
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846657B2

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