Triethylamine → 1-(2-isopropylphenyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzyl)thiourea

HRID 62060Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 62060
Cl.[F:2][C:3]([F:25])([F:24])[O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[N:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][NH2:23])=[CH:18][CH:17]=3)=[N:12]2)=[CH:7][CH:6]=1.C(N(CC)CC)C.[CH:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[N:42]=[C:43]=[S:44])([CH3:35])[CH3:34]>ClCCl>[CH:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[NH:42][C:43]([NH:23][CH2:22][C:19]1[CH:20]=[CH:21][C:16]([C:13]2[N:14]=[CH:15][N:11]([C:8]3[CH:7]=[CH:6][C:5]([O:4][C:3]([F:2])([F:24])[F:25])=[CH:10][CH:9]=3)[N:12]=2)=[CH:17][CH:18]=1)=[S:44])([CH3:35])[CH3:34]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 1420522-Isopropylphenyl isothiocyanateHCID 118675148(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl) methanamine hydrochloride

Produkt 1

HCID 1186750431-(2-isopropylphenyl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzyl)thioureaAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

In a 100 mL flask, to a solution of (4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl) methanamine hydrochloride (0.200 g, 0.598 mmol) in dichloromethane (5 mL) was added triethylamine (0.0720 g, 0.718 mmol) and 1-isopropyl-2-isothiocyanatobenzene (0.106 g, 0.598 mmol) in dichloromethane (5 mL) and the reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated and the residue purified by flash column chromatography eluting with 10-100% ethyl acetate/B, where B=1:1 dichloromethane/hexanes as eluent to give the title compound as a white solid (0.145 g, 48%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified by flash column chromatography
  3. washeluting with 10-100% ethyl acetate/B, where B=1:1 dichloromethane/hexanes as eluent

Quellen und Nachweise

ORD-Eintrag
ord-e991ed1b285e4aeea90a05925aa3c9b5
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09445594B2

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