1-Bromo-2-methylpropane → 2-((4-chlorophenoxy)methyl)-1-isobutyl-1H-benzo[d]imidazole

HRID 537300

Reaktionsgleichung

Reaktionsgleichung von HRID 537300
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].[CH3:25][CH:26]([CH3:29])[CH2:27]Br>CN(C=O)C>[CH3:25][CH:26]([CH3:29])[CH2:27][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 3939882-[(4-chlorophenoxy)methyl]-1H-1,3-benzodiazole

Produkt 1

HCID 7121812-((4-chlorophenoxy)methyl)-1-isobutyl-1H-benzo[d]imidazoleAusbeute 95,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 52 (5.17 g, 0.02 mol) in DMF (50 mL) was added K2CO3 (5.53 g, 0.04 mol) followed by addition of 2-methylpropyl bromide (5.2 g, 0.038 mol) under Ar. The resulting mixture was stirred at rt for 48 hr. HPLC analysis showed that the reaction was not complete. The reaction mixture was further heated at 90° C. for 8 hr, at which point HPLC analysis showed the reaction was complete. The reaction mixture was cooled to rt and filtered. The filter cake was washed with EtOAc (100 mL). The filtrate was washed with H2O (2×75 mL) and brine (100 mL), filtered through phase separation filter paper, and concentrated in vacuo to give an oil (6 g) which solidified. The solid was triturated with hexanes (50 mL), filtered, washed with hexanes (25 mL), and dried to give 4.25 g (80%) of Compound #4. HPLC analysis showed a purity of 100%. 1H NMR (300 MHz, CDCl3): δ 7.85 (m, 1H), 7.45-7.25 (m, 5H), 7.05 (m. 2H), 5.4 (s, 2H), 4.1 (d, 2H), 2.35 (m, 1H), 1.0 (d, 6H) ppm.

Aufarbeitung

  1. temperatureThe reaction mixture was further heated at 90° C. for 8 hr, at which point HPLC analysis
  2. temperatureThe reaction mixture was cooled to rt
  3. filtrationfiltered
  4. washThe filter cake was washed with EtOAc (100 mL)
  5. washThe filtrate was washed with H2O (2×75 mL) and brine (100 mL)
  6. filtrationfiltered through phase separation
  7. filtrationfilter paper
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-68369db91f7849c48785a171cbb2fa90
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859780B2

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