Dicyclohexylcarbodiimide → N-(4-bromophenyl)-6-(trifluoromethyl)-1H-benzimidazol-2-amine

HRID 30897

Reaktionsgleichung

Reaktionsgleichung von HRID 30897
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH2:12].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=S)=[CH:16][CH:15]=1.C1(N=C=NC2CCCCC2)CCCCC1>C1(C)C=CC=CC=1>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[NH:1][C:2]3[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=3[N:12]=2)=[CH:16][CH:15]=1

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 161334-Bromophenyl isothiocyanateHCID 5208224-Trifluoromethyl-1,2-phenylenediamine

Produkt 1

HCID 21985819N-(4-bromophenyl)-6-(trifluoromethyl)-1H-benzimidazol-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

1,2-Diamino-5-trifluoromethylbenzene (0.25 g, 1.42 mmol) was diluted in toluene (5 mL) and treated with 4-bromophenylisothiocyanate (0.30 g, 1.42 mmol). The dark solution was stirred at 100° C. for 15 minutes, then treated with 1,3-dicyclohexylcarbodiimide (0.44 g, 2.13 mmol). The reaction was maintained at 100° C. for 5 h. The reaction was concentrated and partitioned between ethyl acetate and water. The organic layer was separated, dried (MgSO4), and concentrated under reduced pressure. The dark brown oil was purified by flash chromatography on silica gel, eluting with a gradient from 9:1 hexanes/ethyl acetate to 100% ethyl acetate. The title compound was obtained as a light pink solid (0.50 g, 30%). 1H NMR (300 MHz, DMSO-d6) δ 11.3 (broad d, 1H), 9.87 (d, 1H), 7.50 (d, 2H), 7.61 (d, 1H), 7.55-7.42 (m, 3H), 7.35-7.30 (m, 1H); LC/MS m/z 356.2 (MH+), retention time 2.33 minutes.

Aufarbeitung

  1. temperatureThe reaction was maintained at 100° C. for 5 h
  2. concentrationThe reaction was concentrated
  3. custompartitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe dark brown oil was purified by flash chromatography on silica gel
  8. washeluting with a gradient from 9:1 hexanes/ethyl acetate to 100% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-872e5348f1b346b094f0d6394ac9cd56
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423156B2

Verknüpfte Notizen

Wird geladen…