Benzenesulfonamide → HCID 53965777, compound

HRID 466912Notes

Reaction equation

HRID 466912 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([O:16][CH:17]([CH3:21])[C:18]([OH:20])=O)[N:10]=1.[I-].ClC1C=CC=C[N+]=1C.[C:31]1([S:37]([NH2:40])(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(#N)C>[CH3:15][C:13]1[CH:14]=[C:9]([CH3:8])[N:10]=[C:11]([O:16][CH:17]([CH3:21])[C:18]([NH:40][S:37]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(=[O:39])=[O:38])=[O:20])[N:12]=1

Participants

6

Reactant 4

HCID 7370BenzenesulfonamideHCID 8471Triethylamine2×HCID 1670692-Chloro-1-methylpyridinium iodideHCID 19747149HCID 19747149, compound

Product 1

HCID 53965777HCID 53965777, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Triethylamine (2.84 g, 0.028 mol) was added to 2.00 g (0.0102 mol) of the product of (b) in dry acetonitrile (100 ml) and then, at 50° C., 3.00 g, 0.0118 mol, of 2-chloro-N-methyl pyridinium iodide was also added. The mixture was stirred at 50° C. for 30 minutes and then 3.32 g (0.0212 mol) of benzene sulphonamide and 1.42 g (0.014 mol) of triethylamine were added and the stirring continued at 50° C. for a further 30 minutes. The mixture was allowed to cool to ambient temperature (~20° C.) and left overnight, stirring being maintained for the entire period. The acetonitrile was then removed by evaporation, 50 ml of water added, the mixture acidified to a pH of 2, 50 ml of diethyl ether added and the solution vigorously stirred for 1 hour. The desired product, a beige solid, formed and was filtered off and dried.

Workup

  1. waitthe stirring continued at 50° C. for a further 30 minutes
  2. temperatureto cool to ambient temperature (~20° C.)
  3. waitleft overnight
  4. stirringstirring
  5. temperaturebeing maintained for the entire period
  6. customThe acetonitrile was then removed by evaporation, 50 ml of water
  7. additionadded
  8. additionadded
  9. stirringthe solution vigorously stirred for 1 hour

Sources & evidence

ORD record
ord-21c1dfabb00d4d2f96d7ece961f6dde4
Source dataset
uspto-grants-1992_10
Patent number
US05158599

Reaction notes

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