Methyl iodide → Methyl-(3-nitro-4-propyl-phenyl)-carbamic acid tert-butyl ester

HRID 401364Notes

Reaction equation

HRID 401364 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH3:16])=[C:10]([N+:17]([O-:19])=[O:18])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:21]I>CN(C=O)C>[C:1]([O:5][C:6](=[O:20])[N:7]([CH3:21])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH3:16])=[C:10]([N+:17]([O-:19])=[O:18])[CH:9]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 66675112Tert-butyl 3-nitro-4-propylphenylcarbamate

Product 1

HCID 66676075Methyl-(3-nitro-4-propyl-phenyl)-carbamic acid tert-butyl esterYield 52.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3-nitro-4-propyl-phenyl)-carbamic acid tert-butyl ester (200 mg, 0.71 mmol) in DMF (5 mL) was added Ag2O (1.0 g, 6.0 mmol) followed by methyl iodide (0.20 mL, 3.2 mmol). The resulting suspension was stirred at room temperature for 18 h and filtered through a pad of Celite. The filter cake was washed with CH2Cl2 (10 mL). The filtrate was concentrated in vacuo. The crude oil was purified by column chromatography (0-10% CH2Cl2-MeOH) to afford methyl-(3-nitro-4-propyl-phenyl)-carbamic acid tert-butyl ester as a yellow oil (110 mg, 52%). 1H NMR (CDCl3, 300 MHz) δ 7.78 (d, J=2.2 Hz, 1H), 7.42 (dd, J=8.2, 2.2 Hz, 1H), 7.26 (d, J=8.2 Hz, 1H), 3.27 (s, 3H), 2.81 (t, J=7.7 Hz, 2H), 1.66 (m, 2H), 1.61 (s, 9H), 0.97 (t, J=7.4 Hz, 3H).

Workup

  1. filtrationfiltered through a pad of Celite
  2. washThe filter cake was washed with CH2Cl2 (10 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe crude oil was purified by column chromatography (0-10% CH2Cl2-MeOH)

Sources & evidence

ORD record
ord-20b2bd0ec4fe4feb9c88584e261fb8e9
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Reaction notes

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