N-Iodosuccinimide → HCID 69077347, Verbindung

HRID 1916623Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1916623
C([Li])CCC.[CH3:6][N:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH2:16][N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:15][C:10]=2[N:9]=[CH:8]1.[I:22]N1C(=O)CCC1=O>CCCCCC.C1COCC1>[I:22][C:8]1[N:7]([CH3:6])[C:11]2[CH:12]=[CH:13][C:14]([CH2:16][N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:15][C:10]=2[N:9]=1

Komponenten

6

Edukt 3

HCID 120273N-IodosuccinimideHCID 67362954HCID 67362954, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 69077347HCID 69077347, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

0.80 mL (1.28 mmol) 1.6 M n-butyllithium solution in hexane are added to a solution, cooled to −75° C., of 250 mg (1.16 mmol) 1-methyl-5-pyrrolidin-1-ylmethyl-1H-benzimidazole in 8 mL THF. The reaction mixture is stirred for 10 min at this temperature and then 288 mg (1.28 mmol) N-iodosuccinimide in 5 mL THF are added. The cooling bath is removed and the reaction stirred for 1 h at RT. 12 mL 0.1 M HCl are added and the aqueous phase is extracted with EtOAc. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac. The purification is carried out by column chromatography on silica gel (gradient: DCM to DCM/MeOH/NH3 9:1:0.1).

Aufarbeitung

  1. customThe cooling bath is removed
  2. stirringthe reaction stirred for 1 h at RT
  3. addition12 mL 0.1 M HCl are added
  4. extractionthe aqueous phase is extracted with EtOAc
  5. dry with materialThe organic phase is dried over MgSO4
  6. customThe purification

Quellen und Nachweise

ORD-Eintrag
ord-203905a7d77046488e114cc9db773bb7
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618132B2

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