Sulfanilamide → HCID 178514729, compound

HRID 840934Notes

Reaction equation

HRID 840934 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, compoundYield 21.9%

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 hours. 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. Inorganics were removed by filtration through a short silica gel column, eluting with DMF. The resulting solution was diluted with an equal volume of ice water, and the suspension was refrigerated overnight. The solid was isolated by filtration and dried to give 36 mg (21%) of the title compound as a yellow solid: 1H NMR (400 MHz, DMSO-d6) (4:1 ratio of Z:E isomers): δ (Z) 11.07 (s, 1H), 10.76 (d, J=12.4 Hz, 1H), 8.67 (d, J=12.5 Hz, 1H), 7.92 (d, J=5.1 Hz, 1H), 7.84 (d, J=7.3 Hz,

Workup

  1. temperatureat reflux for 2 hours
  2. stirringstirred 10 min
  3. filtrationThe resulting solid was filtered
  4. washwashed with water and ethanol
  5. filtrationfiltered
  6. temperatureupon cooling
  7. customInorganics were removed by filtration through a short silica gel column
  8. washeluting with DMF
  9. additionThe resulting solution was diluted with an equal volume of ice water
  10. customThe solid was isolated by filtration
  11. customdried

Sources & evidence

ORD record
ord-2083743d9207452081ccd9f8a8ef33b1
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

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