Dimethyl Sulfoxide → 1-Isopropyl-1-tosylmethyl isocyanide

HRID 632663Notes

Reaction equation

HRID 632663 reaction equation
[C:1]1(C)[C:2]([S:7]([CH2:10][N+:11]#[C-:12])(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[H-].[Na+].Br[C:17]([CH3:19])=[CH2:18].[CH3:20]S(C)=O>C(OCC)C>[N+:11]([CH:10]([S:7]([C:2]1[CH:1]=[CH:6][C:5]([CH3:20])=[CH:4][CH:3]=1)(=[O:8])=[O:9])[CH:17]([CH3:19])[CH3:18])#[C-:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 112022-BromopropeneHCID 24758Sodium hydrideHCID 53627694Toluenesulfonylmethyl isocyanide

Product 1

HCID 534072211-Isopropyl-1-tosylmethyl isocyanideYield 64%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution toluenesulfonylmethyl isocyanide (53 mg, 0.271 mmol) in DMSO (0.27 mL) and diethyl ether (0.27 mL) at room temperature was added NaH (60% suspension in oil, 21.71 mg, 0.543 mmol) in one portion as a solid. The resulting mixture was stirred for 20 min at room temperature after which time 2-bromopropene (0.038 mL, 0.407 mmol) was added and the reaction was stirred at for 1 h and then quenched by addition of water (8 mL) and extracted with EtOAc (8 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting crude material was purified by column chromatography (SiO2, 0-30% EtOAc/Heptane) to afford 1-((l-isocyano-2-methylpropyl)sulfonyl)-4-methylbenzene (41 mg, 0.173 mmol, 64% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.87 (d, J=7.1 Hz, 2H), 7.42 (d, J=7.1 Hz, 2H), 4.34 (s, 1H), 2.74 (s, 1H), 2.48 (s, 3H), 1.19 (dd, J=19.1, 6.6 Hz, 6H).

Workup

  1. additionwas added
  2. customquenched by addition of water (8 mL)
  3. extractionextracted with EtOAc (8 mL)
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude material was purified by column chromatography (SiO2, 0-30% EtOAc/Heptane)

Sources & evidence

ORD record
ord-3bd5668ad768486ab2a0c49027aacf78
Source dataset
uspto-grants-2016_04
Patent number
US09321746B2

Reaction notes

Loading…