Sulfur Dioxide → HCID 14984039, compound

HRID 864721Notes

Reaction equation

HRID 864721 reaction equation
CN(C)CCN(C)C.C([Li])(CC)C.[CH3:14][O:15][C:16]1[CH:28]=[CH:27][CH:26]=[CH:25][C:17]=1[C:18]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[O:19].[S:29](=[O:31])=[O:30].C([O-])(=O)C.[Na+].[NH2:37]OS(O)(=O)=O>C1COCC1.C1CCCCC1>[NH2:37][S:29]([C:25]1[CH:26]=[CH:27][CH:28]=[C:16]([O:15][CH3:14])[C:17]=1[C:18]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[O:19])(=[O:31])=[O:30]

Participants

9

Reactant 6

HCID 1119Sulfur DioxideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 76284hydroxylamine-O-sulfonic acidHCID 346975N,N-diethyl-2-methoxybenzamideHCID 517045Sodium AcetateHCID 178418400CID 53628100

Product 1

HCID 14984039HCID 14984039, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8078CyclohexaneSolvent

Procedure

To a solution of 8.0 ml (0.053 mol) of tetramethylethylenediamine (TMEDA) in 350 ml of THF at -70° C. was added 42 ml (0.055 mol) of a 1.3M solution of s-butyl lithium in cyclohexane and the mixture was stirred for fifteen minutes. To the solution was added dropwise with stirring a solution of 10.36 g (0.050 mol) of 2-methoxy-N,N-diethylbenzamide in 150 ml of THF while maintaining the temperature at -60° C. or below. After stirring for 20 minutes sulfur dioxide was bubbled into the reaction mixture, keeping the reaction temperature below -50° C. until the reaction mixture was acid to wet litmus paper. The mixture was stirred at ambient temperature for two hours, diluted with 450 ml of hexane, and the solid material which had separated was collected, dissolved in 200 ml of water and the mixture treated with 65 g of sodium acetate and 21.5 g (0.19 mol) of hydroxylamine-O-sulfonic acid in portions with stirring. The white solid which separated was collected and dried to give 7.04 g (49%) of 2-aminosulfonyl-6-methoxy-N,N-diethylbenzamide, mp 190°-194.5° C.

Workup

  1. additionTo the solution was added dropwise
  2. temperaturewhile maintaining the temperature at -60° C. or below
  3. customwas bubbled into the reaction mixture
  4. customthe reaction temperature below -50° C.
  5. stirringThe mixture was stirred at ambient temperature for two hours
  6. additiondiluted with 450 ml of hexane
  7. customthe solid material which had separated
  8. customwas collected
  9. dissolutiondissolved in 200 ml of water
  10. stirringwith stirring
  11. customThe white solid which separated
  12. customwas collected
  13. customdried

Sources & evidence

ORD record
ord-e11bf61e08cb4aa39a2f6c186fa8e97e
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Reaction notes

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