Dichloromethane → 1-(1-Isocyanopentane-1-sulfonyl)-4-methylbenzene

HRID 554227Notes

Reaction equation

HRID 554227 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.[CH2:14](I)[CH2:15][CH2:16][CH3:17].ClCCl.[OH-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[N+:11]([CH:10]([S:7]([C:4]1[CH:3]=[CH:2][C:1]([CH3:13])=[CH:6][CH:5]=1)(=[O:8])=[O:9])[CH2:14][CH2:15][CH2:16][CH3:17])#[C-:12]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10962Butyl iodideHCID 14798Sodium HydroxideHCID 161915Tosylmethyl isocyanide

Product 1

HCID 457899461-(1-Isocyanopentane-1-sulfonyl)-4-methylbenzeneYield 86%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent

Procedure

A mixture of p-toluenesulfonylmethyl isocyanide (9.75 g), tetrabutylammonium iodide (3.69 g), 1-butyl iodide (11.3 mL), dichloromethane (100 mL) and 30% aqueous sodium hydroxide solution (100 mL) was stirred at room temperature for 12 hr. The reaction product was diluted with water (200 mL), and extracted with dichloromethane. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained gum-like residue was extracted 3 times with diethyl ether (100 mL). The extract was concentrated under reduced pressure to give the title compound as a colorless oil (yield 10.8 g, 86%).

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. extractionThe obtained gum-like residue was extracted 3 times with diethyl ether (100 mL)
  6. concentrationThe extract was concentrated under reduced pressure

Sources & evidence

ORD record
ord-91cdd8401df645859ef2931e19cb2ae1
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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