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

HRID 570820Notes

Reaction equation

HRID 570820 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-9ac30c72c78f4f89b5b995e75e743155
Source dataset
uspto-grants-2015_05
Patent number
US09023882B2

Reaction notes

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