Tetrahydrofuran → 1-(2-isopropylphenyl)-3-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea

HRID 62035Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 62035
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[N:12][C:11]([C:14]3[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=3)=[N:10]2)=[CH:5][CH:4]=1.O1CCCC1.[CH:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[N:37]=[C:38]=[S:39])([CH3:30])[CH3:29]>ClCCl>[CH:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[NH:37][C:38]([NH:18][C:17]1[CH:19]=[CH:20][C:14]([C:11]2[N:12]=[CH:13][N:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:21])[F:22])=[CH:8][CH:7]=3)[N:10]=2)=[CH:15][CH:16]=1)=[S:39])([CH3:30])[CH3:29]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 1420522-Isopropylphenyl isothiocyanateHCID 893731204-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)aniline

Produkt 1

HCID 1186750891-(2-isopropylphenyl)-3-(4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To 4-(1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-3-yl)aniline (0.496 g, 1.63 mmol) in a 25 mL vial equipped with a stir bar, Vigreux column, and nitrogen inlet was added tetrahydrofuran (4.08 mL) followed by 1-isopropyl-2-isothiocyanatobenzene (0.826 ml, 4.89 mmol). The reaction was heated to 65° C. overnight. The reaction was cooled to room temperature. The reaction mixture was diluted with dichloromethane and washed with water. The aqueous layer was extracted with dichloromethane (2×). The organic layers were poured through a phase separator and concentrated. Purification by flash column chromatography using 0-20% ethyl acetate/B, where B=1:1 dichloromethane/hexanes as eluent provided a white solid. The solid was dried at 55° C. at about 25 in. Hg providing the title compound as a white solid (0.361 g, 46%).

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. washwashed with water
  3. extractionThe aqueous layer was extracted with dichloromethane (2×)
  4. additionThe organic layers were poured through a phase separator
  5. concentrationconcentrated
  6. customPurification by flash column chromatography
  7. customprovided a white solid
  8. customThe solid was dried at 55° C. at about 25 in

Quellen und Nachweise

ORD-Eintrag
ord-4f80aa5ae11e477b9b17ac7a3839abac
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09445594B2

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