Methylamine → ([2-(Methylamino)ethyl]sulfonyl)benzene

HRID 745169Notes

Reaction equation

HRID 745169 reaction equation
Cl[CH2:2][CH2:3][S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:6])=[O:5].[CH3:13][NH2:14]>C(#N)C>[CH3:13][NH:14][CH2:2][CH2:3][S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:6])=[O:5]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 13646((2-Chloroethyl)sulphonyl)benzene

Product 1

HCID 5152138([2-(Methylamino)ethyl]sulfonyl)benzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-chloroethylphenyl sulfone and a large excess of methylamine (40% solution in water) in acetonitrile is stirred at room temperature overnight. The solvent is removed in vacuo and the residue is partitioned between methylene chloride and dilute sodium hydroxide. The methylene chloride solution is extracted with dilute sulfuric acid. The acidic extract is made basic with 50% sodium hydroxide and the basic solution is extracted with methylene chloride. The methylene chloride solution is dried over magnesium sulfate and the solvent is removed in vacuo to give the title compound.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is partitioned between methylene chloride and dilute sodium hydroxide
  3. extractionThe methylene chloride solution is extracted with dilute sulfuric acid
  4. extractionThe acidic extract
  5. extractionthe basic solution is extracted with methylene chloride
  6. dry with materialThe methylene chloride solution is dried over magnesium sulfate
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-4bcb9985990d4f0a9ba58e9444d206e9
Source dataset
uspto-grants-1986_07
Patent number
US04597902

Reaction notes

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