Methyl iodide → 4-Fluoro-2-(4,4,5-trimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)benzonitrile

HRID 1093039Notes

Reaction equation

HRID 1093039 reaction equation
[CH3:1][C:2]1([CH3:18])[NH:6][S:5](=[O:8])(=[O:7])[N:4]([C:9]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:10]=2[C:11]#[N:12])[CH2:3]1.[H-].[Na+].I[CH3:22]>CN(C=O)C.O>[F:17][C:15]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([N:4]2[CH2:3][C:2]([CH3:18])([CH3:1])[N:6]([CH3:22])[S:5]2(=[O:8])=[O:7])[CH:16]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 579049732-(4,4-Dimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-4-fluorobenzonitrile

Product 1

HCID 579049514-Fluoro-2-(4,4,5-trimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)benzonitrileYield 100.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4,4-dimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-4-fluorobenzonitrile (3.18 g, 11.81 mmol) in DMF (40 mL) was added NaH (0.312 g, 12.99 mmol) and the mixture stirred for 5 min. Iodomethane (1.477 mL, 23.62 mmol) was added and the mixture stirred at 90° C. for 2 h then at room temperature for 16 h. The mixture was diluted with H2O and extracted with ethyl acetate. The organic phase was washed two times with H2O followed by brine, dried (Na2SO4), filtered and concentrated to give the title compound as a white solid (3.35 g, 100% yield). LCMS (M+H) calcd for C12H15FN3O2S: 284.08; found: 284.14. 1H NMR (300 MHz, CDCl3) δ: 7.70-7.61 (2H, m), 7.11-7.05 (1H, m), 3.80 (2H, s), 2.73 (3H, s), 1.42 (6H, s).

Workup

  1. stirringthe mixture stirred at 90° C. for 2 h
  2. waitat room temperature for 16 h
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed two times with H2O
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-94a8b135ff974b0fad4d9272571a95b8
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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