Water → HCID 57687737, compound

HRID 1670871Notes

Reaction equation

[SH:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.F[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[OH2:28]>CN(C)C=O>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([N:3]2[CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=[C:2]2[S:1][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:20])=[O:28])=[CH:15][CH:14]=2)=[CH:14][CH:15]=1)([O-:21])=[O:20]

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 2-mercapto-1H-imidazole-4-carboxylate (1.00 g), 1-fluoro-4-nitrobenzene (2.05 g) and anhydrous potassium carbonate (4.00 g) were mixed in N,N-dimethylformamide (30 mL), and the mixture was stirred at 100° C. for 4 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Diisopropyl ether was added to the residue and the resulting crystals were collected by filtration to give the title compound as pale-yellow crystals (yield 2.06 g, 86%). 1H-NMR (CDCl3) δ: 1.43 (3H, t, J=7.2 Hz), 4.46 (2H, q, J=7.2 Hz), 7.21-7.26 (2H, m), 7.46-7.51 (2H, m), 8.01 (1H, s) 8.07-8.11 (2H, m), 8.31-8.36 (2H, m).

Workup

temperatureThe reaction mixture was cooled
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
additionDiisopropyl ether was added to the residue
filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record: ord-b8d78a0201384739bfff3d76e9c5c05e
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994205B2

Reaction notes

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