Methyl iodide → N-Methyl-N-(2-(morpholine-4-carbonyl)-5-nitrophenyl)methanesulfonamide

HRID 2044100Notes

Reaction equation

HRID 2044100 reaction equation
I[CH3:2].[N:3]1([C:9]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=2[NH:20][S:21]([CH3:24])(=[O:23])=[O:22])=[O:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[H-].[Na+]>CN(C=O)C>[CH3:2][N:20]([C:12]1[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:11]=1[C:9]([N:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)=[O:10])[S:21]([CH3:24])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66833433N-(2-(Morpholine-4-carbonyl)-5-nitrophenyl)methanesulfonamide

Product 1

HCID 66833063N-Methyl-N-(2-(morpholine-4-carbonyl)-5-nitrophenyl)methanesulfonamideYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodomethane (0.040 mL, 0.643 mmol) was added to a solution of N-(2-(morpholine-4-carbonyl)-5-nitrophenyl)methanesulfonamide (108 mg, 0.321 mmol) and 60% suspension of NaH (16.5 mg, 0.413 mmol) in DMF (0.5 mL) at room temperature. After 1.5 h at room temperature, the mixture was carefully quenched with water (10 mL) and extracted with EtOAc (3×4 mL). The combined EtOAc phase was concentrated, purified by silica gel chromatography, and eluted with 10-100% EtOAc in hexanes to give a yellow oil (101.3 mg, 92% yield). LCMS: (M+H)+=344.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.39 (1H, d, J=2.26 Hz), 8.27 (1H, dd, J=8.53, 2.26 Hz), 7.71 (1H, d, J=8.53 Hz), 3.69-3.78 (2H, m), 3.47-3.61 (4H, m), 3.10-3.30 (2H, m), 3.21 (3H, s), 3.17 (3H, s).

Workup

  1. customthe mixture was carefully quenched with water (10 mL)
  2. extractionextracted with EtOAc (3×4 mL)
  3. concentrationThe combined EtOAc phase was concentrated
  4. custompurified by silica gel chromatography
  5. washeluted with 10-100% EtOAc in hexanes

Sources & evidence

ORD record
ord-a50541fbf0954a9e8fe9e64cac97418c
Source dataset
uspto-grants-2013_11
Patent number
US08586751B2

Reaction notes

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