Dicyclohexylcarbodiimide → HCID 178418733, Verbindung

HRID 9583

Reaktionsgleichung

Reaktionsgleichung von HRID 9583
[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)=[C:16]([F:23])[CH:15]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[NH:12][C:3]3[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=3[N:1]=2)=[C:16]([F:23])[CH:15]=1

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 5208224-Trifluoromethyl-1,2-phenylenediamineHCID 27570034-Bromo-2-fluorophenylisothiocyanate

Produkt 1

HCID 178418733HCID 178418733, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

1,2-Diamino-5-trifluoromethylbenzene (0.50 g, 2.84 mmol) was diluted in dichloromethane (5 mL) and treated with 4-bromo-2-fluoro-phenylisothiocyanate (0.66 g, 2.84 mmol). The dark solution was stirred at 45° C. for 15 minutes, then 1,3-dicyclohexylcarbodiimide (0.44 g, 2.13 mmol) was added all at once. The reaction was heated in a 45° C. oil bath overnight, then cooled and concentrated at reduced pressure. The dark residue was diluted with ethyl acetate, and the organic layer was washed with water. The organic layer was dried (MgSO4) and concentrated in vacuo. The resulting dark brown oil was purified by flash chromatography on silica gel eluted on a gradient from 9:1 hexanes/ethyl acetate to 100% ethyl acetate. The title compound was collected as a light pink solid (0.60 g, 57%). 1H NMR (300 MHz, DMSO-d6) δ 11.3 (broad d, 1H), 9.87 (d, 1H), 7.50 (d, 2H), 7.61 (d, 1H), 7.55–7.41 (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 heated in a 45° C. oil bath overnight
  2. temperaturecooled
  3. concentrationconcentrated at reduced pressure
  4. additionThe dark residue was diluted with ethyl acetate
  5. washthe organic layer was washed with water
  6. dry with materialThe organic layer was dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting dark brown oil was purified by flash chromatography on silica gel
  9. washeluted on a gradient from 9:1 hexanes/ethyl acetate to 100% ethyl acetate
  10. customThe title compound was collected as a light pink solid (0.60 g, 57%)

Quellen und Nachweise

ORD-Eintrag
ord-66414de28ead4eef90b6009cd06980d8
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091228B2

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