4-Nitrobenzoyl chloride → N-dodecyl-4-nitrobenzamide
Reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].CCN(C(C)C)C(C)C.[CH2:22]([NH2:34])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>C(Cl)Cl>[CH2:22]([NH:34][C:8](=[O:9])[C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
At 0° C., to a solution of 4-nitro-benzoyl chloride (12.664 g, 68.25 mmol) and DIEA (9.7 g, 75.05 mmol) in anhydrous DCM (200 mL) was added dropwise a solution of dodecylamine (12.650 g, 68.25 mmol in 50 mL of DCM). The reaction mixture was stirred at 0° C. for 30 min, then 1.5 h at rt. The solvents were evaporated and the residue dissolved in boiling AcOEt, washed with water, a 10% aqueous solution of HCl, water, dried over MgSO4 and filtered. The solvents were evaporated to give a yellow solid (23.02 g). This residue was washed twice with diethylether (50 mL) to give after evaporation of the solvent the title compound as a pale yellow powder (20.31 g, 89%). 1H NMR (DMSO-d6, 300 MHz) δ 8.77 (t, 1H, J=5.5 Hz), 8.30 (d, 2H, J=9.0 Hz), 8.04 (d, 2H, J=9.0 Hz), 3.25 (q, 2H, J=6.3 Hz), 1.43-1.58 (m, 2H), 1.12-1.35 (m, 18H), 0.83 (t, 3H, J=6.7 Hz). HPLC (Condition A), Rt: 6.55 min (HPLC purity: 93.2%).
Workup
- custom1.5 h
- customat rt
- customThe solvents were evaporated
- dissolutionthe residue dissolved
- washwashed with water
- dry with materiala 10% aqueous solution of HCl, water, dried over MgSO4
- filtrationfiltered
- customThe solvents were evaporated
Sources & evidence
- ORD record
- ord-1ea95005ce8f4b4ca3e5e561aef595d6
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07592477B2
Reaction notes
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