1-Chloro-2-isothiocyanatobenzene → 4-(2-Chlorophenyl)-1-[3-(3-trifluoromethylbenzamido)-benzoyl]thiosemicarbazide

HRID 970273Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 970273
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12]([NH:14][NH2:15])=[O:13])=[O:7].[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]=[C:32]=[S:33]>O1CCCC1>[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH:31][C:32](=[S:33])[NH:15][NH:14][C:12](=[O:13])[C:11]1[CH:16]=[CH:17][CH:18]=[C:9]([NH:8][C:6](=[O:7])[C:5]2[CH:19]=[CH:20][CH:21]=[C:3]([C:2]([F:22])([F:23])[F:1])[CH:4]=2)[CH:10]=1

Komponenten

4

Edukt 2

HCID 1231711-Chloro-2-isothiocyanatobenzeneHCID 694126823-(3-Trifluoromethylbenzamido)benzhydrazide

Produkt 1

HCID 587259504-(2-Chlorophenyl)-1-[3-(3-trifluoromethylbenzamido)-benzoyl]thiosemicarbazideAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 200 mg (0.62 mmol) of 3-(3-trifluoromethylbenzamido)benzhydrazide in 2.5 mL of tetrahydrofuran was added 157 mg (121 μL, 0.93 mmol) of 2-chlorophenyl isothiocyanate. The reaction was stirred at room temperature overnight. After concentration by rotoevaporation, the residue was purified by preparative HPLC to give 219 mg (0.44 mmol, 72% yield) of 4-(2-chlorophenyl)-1-[3-(3-trifluoromethylbenzamido)-benzoyl]thiosemicarbazide. 1H NMR (CDCl3): δ7.28 (d of t, 1H), 7.36 (d of t, 1H), 7.49 (d of d, 1H), 7.55 (t, 1H), 7.69 (d, 2H), 7.74 (t, 1H), 7.94 (d of t, 2H), 8.21 (d, 1H), 8.27 (s, 1H), 8.36 (s, 1H), and 9.09 ppm (s, 1H). MS m/z: 493.0 (M+H).

Aufarbeitung

  1. concentrationAfter concentration by rotoevaporation
  2. customthe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-0c4d12b9266749199fecbffc30655671
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312181B2

Notizen zur Reaktion

Wird geladen…