p-Fluoronitrobenzene → HCID 18543946, compound

HRID 1268065Notes

Reaction equation

[C:1]1([C:7]2[S:8][C:9]([C:12]3[NH:13][CH:14]=[CH:15][N:16]=3)=[N:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C(OCC)(=O)C>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([N:13]2[CH:14]=[CH:15][N:16]=[C:12]2[C:9]2[S:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:11][N:10]=2)=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-[2-(phenyl)-1,3,4-thiadiazol-5-yl]-1H-imidazole (0.285 g, 1.25 mmol), 1-fluoro-4-nitrobenzene (0.176 g, 1.25 mmol) and sodium carbonate (0.265 g, 2.50 mmol) in DMF (10 mL) was heated at 120° C. for 24 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate and washed with water and brine. The combined organic fraction was dried (Na2SO4) and evaporated to dryness. The crude product was purified by chromatography on silica gel using hexane/ethyl acetate as an eluant to give the product (0.38 g, 87%) as a white solid; 1H NMR δ (DMSO-d6) 8.38 (2H, d, J=8.9 Hz), 7.98 (2H, dd, J=7.7, 1.6 Hz), 7.86 (2H, dd, J=8.8, 1.6 Hz), 7.81 (1H, s), 7.55 (3H, m), 7.43 (1H, dd, J=1.3 Hz); 13C NMR δ (DMSO-d6) 167.8, 159.1, 147.3, 142.6, 136.6, 131.6, 131.0, 129.5, 129.0, 128.1, 127.7, 126.2, 124.3; MS (m/z): 350.4 (M+, 100%).

Workup

temperatureThe reaction mixture was cooled to room temperature
washwashed with water and brine
dry with materialThe combined organic fraction was dried (Na2SO4)
customevaporated to dryness
customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-92fcb2a4963c462b8f46b8f5608dbbcf
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06555563B1

Reaction notes

Loading…