Methanesulfonyl chloride → N-mesyl-O-(p-methoxybenzyl)hydroxylamine

HRID 328356

Reaction equation

HRID 328356 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[CH3:6][O:7][C:8]1[CH:16]=[CH:15][C:11]([CH2:12][O:13][NH2:14])=[CH:10][CH:9]=1>N1C=CC=CC=1>[S:1]([NH:14][O:13][CH2:12][C:11]1[CH:15]=[CH:16][C:8]([O:7][CH3:6])=[CH:9][CH:10]=1)([CH3:4])(=[O:3])=[O:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 120426O-((4-Methoxyphenyl)methyl)hydroxylamine

Product 1

HCID 12763343N-mesyl-O-(p-methoxybenzyl)hydroxylamineYield 64.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

63.0 g (0.55 mole) of mesyl chloride was added dropwise to a solution of 76.5 g (0.5 mole) of O-(p-methoxybenzyl)-hydroxylamine in 400 ml of pyridine while ice-cooling and stirring. After completion of the addition, the resulting mixture was stirred at room temperature (about 20°-30° C) for 5 hours and then the solvent was removed by distillation. 600 ml of ethyl acetate was added to the resulting residue, and the mixture was washed successively with 1N hydrochloric acid and water. The mixture was then dried and the solvent was distilled off to obtain 75 g (64.8% yield) of N-mesyl-O-(p-methoxybenzyl)hydroxylamine (IV) having a melting point of 114°-116° C.

Workup

  1. temperaturecooling
  2. additionAfter completion of the addition
  3. stirringthe resulting mixture was stirred at room temperature (about 20°-30° C) for 5 hours
  4. customthe solvent was removed by distillation
  5. addition600 ml of ethyl acetate was added to the resulting residue
  6. washthe mixture was washed successively with 1N hydrochloric acid and water
  7. customThe mixture was then dried
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-663826d4311c464fab7daaf518a53796
Source dataset
uspto-grants-1977_04
Patent number
US04017512

Linked notes

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