Acetic Acid → N2-Mesityl-1-methyl-N7,N7-dipropyl-1H-benzimidazole-2,7-diamine

HRID 2235534Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2235534
[C:1]1([CH3:21])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH:9][C:10]1[N:14]([CH3:15])[C:13]2[C:16]([NH2:20])=[CH:17][CH:18]=[CH:19][C:12]=2[N:11]=1.[CH:22](=O)[CH2:23][CH3:24].[BH3-][C:27]#N.[Na+].[C:30](O)(=O)[CH3:31]>CO.C(OCC)(=O)C>[C:1]1([CH3:21])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH:9][C:10]1[N:14]([CH3:15])[C:13]2[C:16]([N:20]([CH2:27][CH2:30][CH3:31])[CH2:22][CH2:23][CH3:24])=[CH:17][CH:18]=[CH:19][C:12]=2[N:11]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 527PropanalHCID 5003444Sodium cyanoborohydrideHCID 86049130N2-Mesityl-1-methyl-1H-benzimidazole-2,7-diamine

Produkt 1

HCID 11210737N2-Mesityl-1-methyl-N7,N7-dipropyl-1H-benzimidazole-2,7-diamineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution containing 0.05 g (0.18 mmol) of N2-mesityl-1-methyl-1H-benzimidazole-2,7-diamine in methanol (5 ml) was added 0.03 ml (0.54 mmol) of propionaldehyde, 0.03 g (0.54 mmol) of NaBH3CN and 0.1 ml of acetic acid. The mixture was stirred overnight then diluted with ethyl acetate and washed with water. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via Biotage chromatography eluting with 5% methanol/dichloromethane gave 0.04 g (70%) of product.

Aufarbeitung

  1. washwashed with water
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationFiltration, removal of solvent and purification of the residue via Biotage chromatography
  4. washeluting with 5% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-42bcf7ca17e5409bb08b00eaea192bcf
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07714009B2

Notizen zur Reaktion

Wird geladen…