Methyl iodide → N-(3-fluorophenyl)-3-iodo-N-methylbenzamide
Reaction equation
[H-].[Na+].[CH3:3]I.[F:5][C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:21])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([I:20])[CH:15]=2)[CH:9]=[CH:10][CH:11]=1>CN(C=O)C>[F:5][C:6]1[CH:7]=[C:8]([N:12]([CH3:3])[C:13](=[O:21])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([I:20])[CH:15]=2)[CH:9]=[CH:10][CH:11]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Sodium hydride (1.11 g of 60% NaH in mineral oil) was added to a solution of CH3I (4.53 g) and N-(3-fluorophenyl)-3-iodobenzamide (7.26 g) in DMF (120 mL) at 0° C. under nitrogen. After being stirred at 0° C. for another 5 minutes, the reaction was stirred at room temperature under nitrogen for 4 h. The reaction was quenched by slow addition of saturated aqueous NH4Cl (120 mL), followed by addition of water (100 mL). The mixture was extracted with diethyl ether (300 mL×2). The combined ether layers were washed by water (150 mL×4) and brine (150 mL×1), dried by Na2SO4 and concentrated to give crude product (7.56 g), which was purified by column chromatography to afford N-(3-fluoro-phenyl)-3-iodo-N-methylbenzamide (5.88 g; 78%). 1H NMR (600 MHz, DMSO-d6) δ 7.64 (m, 2H), 7.28 (m, 1H), 7.24 (d, 1H, J=7.5 Hz), 7.19 (m, 1H), 7.04-6.99 (m, 3.33 (s, 3H).
Workup
- stirringthe reaction was stirred at room temperature under nitrogen for 4 h
- customThe reaction was quenched by slow addition of saturated aqueous NH4Cl (120 mL)
- additionfollowed by addition of water (100 mL)
- extractionThe mixture was extracted with diethyl ether (300 mL×2)
- washThe combined ether layers were washed by water (150 mL×4) and brine (150 mL×1)
- dry with materialdried by Na2SO4
- concentrationconcentrated
- customto give crude product (7.56 g), which
- customwas purified by column chromatography
Sources & evidence
- ORD record
- ord-105fb1e759644ca19426871000b13620
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476280B2
Reaction notes
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