Methyl iodide → HCID 3256951, compound

HRID 2044091Notes

Reaction equation

HRID 2044091 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:9]=[CH:10][CH:11]=1)([O-:5])=[O:4].I[CH3:23]>CN(C=O)C>[CH3:23][N:12]([C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=1)[S:13]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66459N-(m-Nitrophenyl)benzenesulphonamide

Product 1

HCID 3256951HCID 3256951, compoundYield 114.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 60% suspension of NaH (0.47 g, 11.75 mmol) was added to a solution of N-(3-nitrophenyl)benzenesulfonamide (2.56 g, 9.20 mmol) and iodomethane (2.61 g, 18.4 mmol) in DMF (50 mL) at room temperature. The yellow solution changed to a bright brown color. After 1.5 h at room temperature, the reaction mixture was quenched with careful addition of water (100 mL) and extracted with EtOAc (2×50 mL). The combined extracts were washed with saturated NH4Cl, brine, dried (MgSO4) and concentrated to give N-methyl-N-(3-nitrophenyl)benzenesulfonamide (3.09 g). LCMS: (M+MeCN+Na)+=356.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.16 (1H, ddd, J=8.03, 2.26, 1.25 Hz), 7.94 (1H, t, J=2.13 Hz), 7.70-7.76 (1H, m), 7.66 (1H, t, J=8.03 Hz), 7.57-7.62 (3H, m), 7.52-7.56 (2H, m), 3.21 (3H, s).

Workup

  1. customthe reaction mixture was quenched with careful addition of water (100 mL)
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe combined extracts were washed with saturated NH4Cl, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-81610c9d45ec4b0eba74ff704f1b8820
Source dataset
uspto-grants-2013_11
Patent number
US08586751B2

Reaction notes

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