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

HRID 2404757Notes

Reaction equation

HRID 2404757 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-f8e36b11e61747a5aff7a4d11e204fdc
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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