2-Bromo-6-phenylcyclohexanone → [4-(2-Methyl-oxazol-5-yl)-phenyl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine

HRID 2076084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2076084
[CH3:1][C:2]1[O:3][C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH2:16])=[S:15])=[CH:9][CH:8]=2)=[CH:5][N:6]=1.Br[CH:18]1[CH2:23][CH2:22][CH2:21][CH:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]1=O>C(O)C>[CH3:1][C:2]1[O:3][C:4]([C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:14]3[S:15][C:26]4[CH2:27][CH2:28][CH2:29][CH:24]([C:20]5[CH:21]=[CH:22][CH:23]=[CH:18][CH:19]=5)[C:25]=4[N:16]=3)=[CH:11][CH:12]=2)=[CH:5][N:6]=1

Komponenten

4

Edukt 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 86632608[4-(2-Methyl-oxazol-5-yl)-phenyl]-thiourea

Produkt 1

HCID 44193858[4-(2-Methyl-oxazol-5-yl)-phenyl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amineAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of [4-(2-methyl-oxazol-5-yl)-phenyl]-thiourea (100 mg, 0.43 mmol) and 2-bromo-6-phenyl-cyclohexanone (114 mg, 0.45 mmol) in ethanol (5 mL) was heated to reflux over night. The solvent was removed under reduced pressure and the residue purified on silica gel using methylene chloride and methylene chloride/methanol (19:1 v/v) as eluent to yield the title compound (73 mg, 44%) as a yellow gum. MS ISP (m/e): 388.2 (100%) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.18 (s, 1H), 7.49 (m, 4H), 7.11-7.29 (m, 6H), 4.04 (m, 1H), 2.70 (m, 2H), 2.43 (s, 3H), 2.14 (m, 1H), 1.70-1.93 (m, 3H).

Aufarbeitung

  1. temperatureto reflux over night
  2. customThe solvent was removed under reduced pressure
  3. customthe residue purified on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-6875cb15b25f4a42976a261b06b90417
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07923450B2

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