Benzyl Chloride → N-benzyl-N-mesyl-O-(p-methoxybenzyl)hydroxylamine

HRID 328357Notes

Reaction equation

HRID 328357 reaction equation
[S:1]([NH:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)([CH3:4])(=[O:3])=[O:2].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C[O-].[Na+]>[CH2:16]([N:5]([S:1]([CH3:4])(=[O:2])=[O:3])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 7503Benzyl ChlorideHCID 12763343N-mesyl-O-(p-methoxybenzyl)hydroxylamine

Product 1

HCID 12763344N-benzyl-N-mesyl-O-(p-methoxybenzyl)hydroxylamineYield 65.6%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

9.25 g (40 mmoles) of N-mesyl-O-(p-methoxybenzyl)hydroxylamine prepared as described in Reference Example 5 was added to sodium methoxide (prepared from 150 ml of absolute methanol and 1.2 g of sodium metal), and 6 g of benzyl chloride was then added to the mixture. The resulting mixture was heated under refluxing for 3 hours. The solvent was distilled off, and 150 ml of ethyl acetate and 50 ml of water were added to the residue. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated to obtain 8.4 g (65.6% yield) of N-benzyl-N-mesyl-O-(p-methoxybenzyl)hydroxylamine having a melting point of 85°-87° C.

Workup

  1. additionwas then added to the mixture
  2. temperatureThe resulting mixture was heated
  3. temperatureunder refluxing for 3 hours
  4. distillationThe solvent was distilled off
  5. addition150 ml of ethyl acetate and 50 ml of water were added to the residue
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-90c6fd5f3d2b45739de7ce4eb390ee8f
Source dataset
uspto-grants-1977_04
Patent number
US04017512

Reaction notes

Loading…