N-Methylaniline → N-methyl-N-phenyl-1H-imidazole-1-sulfonamide

HRID 1403720Notes

Reaction equation

HRID 1403720 reaction equation
FC(F)(F)S([O-])(=O)=O.[N:9]1([S:14]([N:17]2[CH:21]=[CH:20][N+](C)=[CH:18]2)(=[O:16])=[O:15])[CH:13]=[CH:12][N:11]=[CH:10]1.CN[C:25]1[CH:30]=CC=[CH:27][CH:26]=1>CC#N>[CH3:18][N:17]([C:21]1[CH:20]=[CH:27][CH:26]=[CH:25][CH:30]=1)[S:14]([N:9]1[CH:13]=[CH:12][N:11]=[CH:10]1)(=[O:15])=[O:16]

Participants

4

Reactant 2

HCID 7515N-MethylanilineHCID 117281493-(Imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate

Product 1

HCID 57767786N-methyl-N-phenyl-1H-imidazole-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(1H-imidazol-1-ylsulfonyl)-3-methyl-1H-imidazol-3-ium trifluoromethanesulfonate (3 g, 8.3 mmol) in dry CH3CN (dried over MgSO4) was added N-methylaniline (740 mg, 6.9 mmol) under nitrogen. The mixture was stirred at room temperature for 16 h. After the solvent was removed, the residue was extracted with EtOAc (50 mL×3). The organic layer was washed with brine (50 mL) and water (50 mL). After the solvent was removed, the residue was purified by column chromatography (eluting with 30˜60% EtOAc) to give the title compound, which was used in next step without further purification (1 g, 51%). LCMS (ESI): m/z 237.9 [M+H+].

Workup

  1. customAfter the solvent was removed
  2. extractionthe residue was extracted with EtOAc (50 mL×3)
  3. washThe organic layer was washed with brine (50 mL) and water (50 mL)
  4. customAfter the solvent was removed
  5. customthe residue was purified by column chromatography (eluting with 30˜60% EtOAc)

Sources & evidence

ORD record
ord-ee9e6ca25100488094530ffd2c6bda8e
Source dataset
uspto-grants-2014_12
Patent number
US08912219B2

Reaction notes

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