Carbon Dioxide → N-{[2,4-bis(methyloxy)phenyl]methyl)-2-chloro-5-iodobenzamide
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.C(=O)=O.[CH3:27][O:28][C:29]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:30]=1[CH2:31][NH2:32]>C1COCC1>[CH3:27][O:28][C:29]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:30]=1[CH2:31][NH:32][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([I:11])[CH:9]=[CH:10][C:2]=1[Cl:1]Participants
Procedure
2-Chloro-5-iodobenzoic acid (2 g, 7.08 mmol) in 25 mL THF was treated with 1,1′-carbonyldiimidazole (1.15 g, 7.08 mmol) at ambient temperature until CO2 evolution ceased (˜20 min). 2,4-Dimethoxybenzylamine (1.18 g, 7.08 mmol) was added and stirred at ambient temperature for 16 h. The reaction mixture was concentrated to dryness, partitioned between EtOAc and saturated NaHCO3, the organic phase isolated, dried over MgSO4, filtered and concentrated to give N-{[2,4-bis(methyloxy)phenyl]methyl}-2-chloro-5-iodobenzamide (3.00 g, 6.95 mmol) as a pale yellow oil that crystallized on standing. 1H NMR (300 MHz, CDCl3) d 7.95 (d, J=2.2 Hz, 1H), 7.62 (dd, J=8.5, 2.2 Hz, 1H), 7.25 (m, 1H), 7.10 (m, 1H), 6.63 (m, 1H), 6.45 (m, 2H), 4.55 (d, J=5.7 Hz, 2H), 3.83 (s, 3H), 3.80 (s, 3H). LCMS ES+ 431.82, 433.77 (M+H).
Workup
- custom(˜20 min)
- concentrationThe reaction mixture was concentrated to dryness
- custompartitioned between EtOAc and saturated NaHCO3
- customthe organic phase isolated
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-74753719fad447bb84919ec66cfae8e4
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07645771B2
Reaction notes
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