Methyl iodide → HCID 70003859, compound

HRID 1264385Notes

Reaction equation

HRID 1264385 reaction equation
[CH2:1]([O:8][C:9](=[O:25])[N:10]([CH2:12][C:13](=[O:24])[N:14]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][OH:23])=[CH:18][CH:17]=1)[CH3:15])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:28]I>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:25])[N:10]([CH2:12][C:13](=[O:24])[N:14]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][O:23][CH3:28])=[CH:18][CH:17]=1)[CH3:15])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70000907HCID 70000907, compound

Product 1

HCID 70003859HCID 70003859, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon to 1.23 g (3.6 mmol) [[(4-Hydroxymethyl-phenyl)-methyl-carbamoyl]-methyl]-methyl-carbamic acid benzyl ester in 40 ml DMF were added 580 mg (13.3 mmol, 3.7 eq, 55% disp) sodium hydride, followed by 3.8 ml (59.6 mmol, 16.6 eq) methyl iodide. The suspension was stirred at RT over night, and added to ice water. The layers were separated and the inorganic one was extracted with 50 ml CH2Cl2 (3×). The combined organic layers were washed with water (2×), dried over MgSO4, filtered and evaporated. Column chromatography on silica gel with a gradient of CH2Cl2/MeOH (100:0-98:2) afforded 0.984 g (77%) [[(4-Methoxymethyl-phenyl)-methyl-carbamoyl]-methyl]-methyl-carbamic acid benzyl ester as a light yellow oil (Rf 0.07 CH2Cl2:MeOH 9:1), MS: 356 (M), +), which was deprotected according to 6.1. to give N-(4-Methoxymethyl-phenyl)-N-methyl-2-methylamino-acetamide as yellow oil (Rf 0.2 CH2Cl2:MeOH 9:1), MS: 223 (MH+).

Workup

  1. customThe layers were separated
  2. extractionthe inorganic one was extracted with 50 ml CH2Cl2 (3×)
  3. washThe combined organic layers were washed with water (2×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-70774c602a724577bf89e35eb22a3d3e
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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