Water → HCID 22272449, compound

HRID 346762Notes

Reaction equation

HRID 346762 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:7]=1.CI.[C:18](=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([N:8]([CH3:18])[S:9]([CH3:12])(=[O:10])=[O:11])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 22272570HCID 22272570, compound

Product 1

HCID 22272449HCID 22272449, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

N-(5-fluoro-2-nitrophenyl)methanesulfonamide compound (5 g, 21 mmol), methyl iodide (3 mL) and potassium carbonate (10 g) were stirred together in DMSO (100 mL) at 80° C. overnight. The reaction was not complete and a further 1 mL of methyl iodide was added. After a further 24 hours at 80° C., water (1000 mL) was added. The solution was decanted from a small amount of sticky residue. The product crystallized out from the aqueous solution (48 hours) and was collected by filtration, washed with water and dried. Yield 3.3 g (63%); 1H NMR (400 MHz, CDCl3) δ 3.04 (s, 3H), 3.30 (s, 3H), 7.20 (m, 1H), 7.31 (dd, J=8.54, 2.68 Hz, 1H), 8.0 (dd, J=9.3, 5.6 Hz, 1H); MS (ESI+) for C8H9FN2O4S m/z 248 M+.

Workup

  1. customThe solution was decanted from a small amount of sticky residue
  2. customThe product crystallized out from the aqueous solution (48 hours)
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-44370af5b54e408994bd21a9e662a278
Source dataset
uspto-grants-2007_02
Patent number
US07173035B2

Reaction notes

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