Water → 1-(1-Isocyanoethanesulfonyl)-4-methylbenzene

HRID 1516567Notes

Reaction equation

HRID 1516567 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([S:7]([CH2:10][N+:11]#[C-:12])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:14]I.[OH-].[Na+].O>ClCCl>[C:1]1([CH3:13])[CH:2]=[CH:3][C:4]([S:7]([CH:10]([N+:11]#[C-:12])[CH3:14])(=[O:8])=[O:9])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 161915Tosylmethyl isocyanide

Product 1

HCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzeneYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of toluene-4-sulfonylmethylisocyanide (15 g), methyl iodide (109 g) benzyl trimethyl ammonium chloride (3.5 g) in dichloromethane (300 mL) was added 5 mol/L aqueous sodium hydroxide solution (307 mL) under ice cooling, and this mixture was stirred at same temperature for 2 hours. To this reaction mixture was added water and this mixture was extracted with diethyl ether. This organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (16 g).

Workup

  1. extractionthis mixture was extracted with diethyl ether
  2. washThis organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-34c2e8a16be24403b3e24cb96fc0bfe0
Source dataset
uspto-grants-2012_07
Patent number
US08227500B2

Reaction notes

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