Water → methyl N-methoxy-N-(2-methyl-3-phenylbenzyl)carbamate

HRID 1168034Notes

Reaction equation

HRID 1168034 reaction equation
[CH3:1][O:2][NH:3][C:4](=[O:7])[O:5][CH3:6].[H-].[Na+].[CH3:10][C:11]1[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13]Br.O>CN(C)C=O>[CH3:1][O:2][N:3]([CH2:13][C:12]1[CH:15]=[CH:16][CH:17]=[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:11]=1[CH3:10])[C:4](=[O:7])[O:5][CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 12663380methyl N-methoxycarbamateHCID 147188083-(Bromomethyl)-2-methyl-1,1'-biphenyl

Product 1

HCID 22995021methyl N-methoxy-N-(2-methyl-3-phenylbenzyl)carbamateYield 50.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.40 g of methyl N-methoxycarbamate in N,N-dimethylformamide (20 ml) was stirred together with 0.18 g of 60% sodium hydride at room temperature for 30 minutes. 1.00 g of 2-methyl-3-phenylbenzyl bromide was added dropwise at room temperature, and the resulting solution was stirred for 3 hours. After the reaction, the reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was separated, dried over anhydrous magnesium sulfate and evaporated under reduced pressure for removal of the solvent. The residue was purified by silica gel column chromatography to give 0.55 g of methyl N-methoxy-N-(2-methyl-3-phenylbenzyl)carbamate as a transparent viscous liquid.

Workup

  1. customAfter the reaction
  2. extractionextracted with ethyl acetate
  3. customthe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure for removal of the solvent
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3e3a4554ad7946f8a83c5a48c34ef196
Source dataset
uspto-grants-2003_09
Patent number
US06620961B1

Reaction notes

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