Water → methyl N-methoxymethyl-N-(3-phenylbenzyl)carbamate

HRID 1168031Notes

Reaction equation

HRID 1168031 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][CH:18]=2)[CH2:10][NH:11][C:12](=[O:15])[O:13][CH3:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:21][O:22][CH2:23]Br.O>O1CCCC1>[CH3:21][O:22][CH2:23][N:11]([CH2:10][C:9]1[CH:16]=[CH:17][CH:18]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=1)[C:12](=[O:15])[O:13][CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 83093Bromomethyl methyl etherHCID 12090300methyl N-(3-phenylbenzyl)carbamate

Product 1

HCID 12090306methyl N-methoxymethyl-N-(3-phenylbenzyl)carbamateYield 76.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.00 g of methyl N-(3-phenylbenzyl)carbamate in tetrahydrofuran (20 ml) was stirred together with 0.22 g of 60% sodium hydride at room temperature for 30 minutes. 0.78 g of methoxymethyl bromide was added dropwise at room temperature, and the resulting solution was stirred overnight. 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 0.90 g of methyl N-methoxymethyl-N-(3-phenylbenzyl)carbamate as a pale yellow 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-a241719dc28248dcb5e7c404b29c52ec
Source dataset
uspto-grants-2003_09
Patent number
US06620961B1

Reaction notes

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