4-(1,2,4-Triazol-1-yl)phenylthiourea → (4-Phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-(4-[1,2,4]triazol-1-yl-phenyl)-amine

HRID 2075975

Reaktionsgleichung

Reaktionsgleichung von HRID 2075975
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]([NH2:15])=[S:14])=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.Br[CH:17]1[CH2:22][CH2:21][CH2:20][CH:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:18]1=O>C(O)C>[C:19]1([CH:23]2[C:24]3[N:15]=[C:13]([NH:12][C:9]4[CH:8]=[CH:7][C:6]([N:1]5[CH:5]=[N:4][CH:3]=[N:2]5)=[CH:11][CH:10]=4)[S:14][C:25]=3[CH2:26][CH2:27][CH2:28]2)[CH:20]=[CH:21][CH:22]=[CH:17][CH:18]=1

Komponenten

4

Edukt 2

HCID 52606784-(1,2,4-Triazol-1-yl)phenylthioureaHCID 127791292-Bromo-6-phenylcyclohexanone

Produkt 1

HCID 57399119(4-Phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-(4-[1,2,4]triazol-1-yl-phenyl)-amineAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of 4-(1,2,4-triazol-1-yl)phenylthiourea (109.6 mg, 0.5 mmol) and of 2-bromo-6-phenyl-cyclohexanone (253.1 mg, 1.00 mmol) in ethanol (4 mL) was heated for two days to reflux under an atmosphere of nitrogen. After cooling to room temperature the solvent was evaporated under reduced pressure and the residue was treated with dichloromethane, diethyl ether and heptane. The product precipitated as a solid and was filtered off to yield the title compound (120 mg, 64%) as a pale-brown solid. MS ISP (m/e): 374.3 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.4 (s, 1H), 9.38 (s, 1H), 8.29 (s, 1H), 8.02 (d, 2H), 7.56 (d, 2H), 7.30 (t, 2H), 7.10-7.19 (m, 5H), 4.00 (m, 1H), 2.72 (m, 2H), 2.14 (m, 1.70-1.89 (m, 3H).

Aufarbeitung

  1. temperatureto reflux under an atmosphere of nitrogen
  2. customwas evaporated under reduced pressure
  3. additionthe residue was treated with dichloromethane, diethyl ether and heptane
  4. customThe product precipitated as a solid
  5. filtrationwas filtered off

Quellen und Nachweise

ORD-Eintrag
ord-b010277627c24eb3b246654ff4874675
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07923450B2

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