Sulfanilamide → HCID 178514729, compound

HRID 2414731Notes

Reaction equation

HRID 2414731 reaction equation
[C:1](OC(OC(C)(C)C)N(C)C)(C)(C)C.[NH:15]1[C:19]2=[N:20][CH:21]=[CH:22][CH:23]=[C:18]2[CH2:17][C:16]1=[O:24].[S:25]([NH2:35])(=[O:34])([C:27]1[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=1)=[O:26].CS(O)(=O)=O.C([O-])(O)=O.[Na+]>CN(C=O)C.C(O)C.O>[O:24]=[C:16]1[NH:15][C:19]2=[N:20][CH:21]=[CH:22][CH:23]=[C:18]2[C:17]1=[CH:1][NH:33][C:30]1[CH:29]=[CH:28][C:27]([S:25]([NH2:35])(=[O:34])=[O:26])=[CH:32][CH:31]=1

Participants

9

Reactant 5

HCID 5333SulfanilamideHCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 138640951,3-Dihydro-2H-pyrrolo(2,3-b)pyridin-2-one

Product 1

HCID 178514729HCID 178514729, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Dimethylformamide di-tert-butyl acetal (180 mg, 0.89 mmol) was added to a solution of 1,2-dihydro-3H-pyrrolo[2,3-b]pyridin-2-one (70 mg, 0.52 mmol) in 0.25 ml DMF, and the reaction mixture was slowly warmed to 100° C. The cooled solution was then diluted with 5 ml of ethanol. Sulfanilamide (172 mg, 1.00 mmol) and methanesulfonic acid (60 mg, 0.63 mmol) were added, and the reaction mixture was stirred at reflux for 2 h. The cooled solution was diluted with 4 ml of water, treated with NaHCO3 (70 mg, 0.83 mmol) and stirred 10 min. The resulting solid was filtered, washed with water and ethanol, and then suspended in boiling methanol and filtered upon cooling.

Workup

  1. temperatureat reflux for 2 h
  2. stirringstirred 10 min
  3. filtrationThe resulting solid was filtered
  4. washwashed with water and ethanol
  5. filtrationfiltered
  6. temperatureupon cooling

Sources & evidence

ORD record
ord-4d5fe53e28e347b6814e547d1d683027
Source dataset
uspto-grants-2004_11
Patent number
US06815439B2

Reaction notes

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