Methyl iodide → [5-(2-Benzyloxy-ethoxy)-2-nitro-phenyl]-methyl-carbamic acid methyl ester

HRID 1955251Notes

Reaction equation

HRID 1955251 reaction equation
[CH3:1][O:2][C:3](=[O:25])[NH:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:8]=[CH:7][C:6]=1[N+:22]([O-:24])=[O:23].I[CH3:27].[H-].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:25])[N:4]([C:5]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:8]=[CH:7][C:6]=1[N+:22]([O-:24])=[O:23])[CH3:27]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53935046[5-(2-Benzyloxy-ethoxy)-2-nitro-phenyl]-carbamic acid methyl ester

Product 1

HCID 54555542[5-(2-Benzyloxy-ethoxy)-2-nitro-phenyl]-methyl-carbamic acid methyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of [5-(2-benzyloxy-ethoxy)-2-nitro-phenyl]-carbamic acid methyl ester (2.03 g, 5.86 mmol) in anhydrous dimethylformamide (20 ml) was added iodomethane (1.82 ml, 29.3 mmol), followed by portion wise addition of NaH (0.35 g, 60%, 8.79 mmol). The reaction was stirred under nitrogen for 2 h. The reaction was quenched with NH4Cl (sat) (10 ml) and brine (10 ml), and the aqueous layer was extracted with ether (3×30 ml). The combined organics were dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel eluting with hexanes, then 30% ethyl acetate/hexanes to give [5-(2-benzyloxy-ethoxy)-2-nitro-phenyl]-methyl-carbamic acid methyl ester (0.93 g, 89%) as an oil. Analysis calculated for C18H20N2O6 : C, 59.99; H, 5.59; N, 7.77. Found: C, 59.30; H, 5.34; N, 7.62.

Workup

  1. customThe reaction was quenched with NH4Cl (sat) (10 ml) and brine (10 ml)
  2. extractionthe aqueous layer was extracted with ether (3×30 ml)
  3. dry with materialThe combined organics were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was chromatographed on silica gel eluting with hexanes

Sources & evidence

ORD record
ord-2d6906aa0e4c491e9da7edaf8625f549
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

Loading…