2-Bromo-6-phenylcyclohexanone → [4-(2,4-Dimethyl-thiazol-5-yl)-3-methoxy-phenyl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine

HRID 2076133Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2076133
[CH3:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([NH2:17])=[S:16])=[CH:10][C:9]=2[O:18][CH3:19])=[C:5]([CH3:7])[N:6]=1.Br[CH:21]1[CH2:26][CH2:25][CH2:24][CH:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:22]1=O>C(O)C>[CH3:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[S:16][C:29]4[CH2:30][CH2:31][CH2:32][CH:27]([C:23]5[CH:24]=[CH:25][CH:26]=[CH:21][CH:22]=5)[C:28]=4[N:17]=3)=[CH:10][C:9]=2[O:18][CH3:19])=[C:5]([CH3:7])[N:6]=1

Komponenten

4

Edukt 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 86632613[4-(2,4-Dimethyl-thiazol-5-yl)-3-methoxy-phenyl]-thiourea

Produkt 1

HCID 44193960[4-(2,4-Dimethyl-thiazol-5-yl)-3-methoxy-phenyl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of [4-(2,4-dimethyl-thiazol-5-yl)-3-methoxy-phenyl]-thiourea (88 mg, 0.30 mmol) and 2-bromo-6-phenyl-cyclohexanone (80 mg, 0.32 mmol) in ethanol (3 ml) was heated to reflux over night. The precipitated solid was filtered off after cooling to room temperature and dried to yield the title compound (100 mg, 100%) as a yellow solid. MS ISP (m/e): 448.2 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.27 (br s, 1H, NH), 7.59 (s, 1H), 7.28 (t, 2H), 7.12-7.19 (m, 4H), 6.85 (d, 1H), 4.00 (m, 1H), 3.37 (s, 3H), 2.74 (m, 2H), 2.66 (s, 3H), 2.20 (s, 2H), 2.13 (m, 1H), 1.70-1.93 (m, 3H).

Aufarbeitung

  1. temperatureto reflux over night
  2. filtrationThe precipitated solid was filtered off
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d04d7e206a2040e7a43548a31c314d87
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07923450B2

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