Pyridine → 5-[1-(6-Methoxy-2-naphthyl)ethyl]-2-phenyl-4-hydroxythiazole

HRID 1086808Notes

Reaction equation

Br[CH:2]([CH:6]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=2)[CH:9]=1)[CH3:7])[C:3](Br)=[O:4].[C:20]([NH2:28])(=[S:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:19][O:18][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:6]([C:2]1[S:27][C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:28][C:3]=1[OH:4])[CH3:7])[CH:17]=[CH:16]2

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-bromo-3-(6-methoxy-2-naphthyl) butyrylbromide (386 mg, 1 mmol) in toluene (20 mL) was added thiobenzamide (137 mg, 1 mmol) and pyridine (0.16 mL, 2 mmol) in toluene (60 mL) at 23° C. The reaction mixture was heated at 100° C. for 4 hours and then cooled and the solvent removed in vacuo. Recrystallization of the residue from ethanol/ether provided the desired product (128 mg). mp 224°-226° C., 1H NMR (60 MHz, DMSO-d6) 1.30 (3H, d, J=7 Hz), 3.82 (3H, s), 3.92 (1H, g, J=7 Hz), 7.1-8.0 (11H, m), 10.55 (1H, s); Mass Spectrum: 361 (M+).

Workup

temperaturecooled
customthe solvent removed in vacuo
customRecrystallization of the residue from ethanol/ether

Sources & evidence

ORD record: ord-e85cd79f4fa4446ab7a9e78ef00c28d1
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05032588

Reaction notes

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