Sulfanilamide → HCID 178514728, compound

HRID 840933Notes

Reaction equation

HRID 840933 reaction equation
C[N:2]([CH:4]=[C:5]1[C:13]2[C:8](=[CH:9][N:10]=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:14])[CH3:3].[S:15]([NH2:25])(=[O:24])([C:17]1[CH:22]=[CH:21]C(N)=[CH:19][CH:18]=1)=[O:16]>Cl.C(O)C>[O:14]=[C:6]1[NH:7][C:8]2=[CH:9][N:10]=[CH:11][CH:12]=[C:13]2[C:5]1=[CH:4][NH:2][C:3]1[CH:21]=[CH:22][C:17]([S:15]([NH2:25])(=[O:24])=[O:16])=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 5333SulfanilamideHCID 57201379HCID 57201379, compound

Product 1

HCID 178514728HCID 178514728, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

To a 25-ml round-bottom flask was added 0.12 g (0.47 mmol) of 3-dimethylaminomethylene-1,6-diazainden-2(3H)-one, 0.081 g (0.47 mmol) of sulfanilamide, 10 ml of ethanol and two drops of concentrated hydrochloric acid. The reaction mixture was refluxed using an oil bath with stirring for 3 hours, then cooled and filtered. The collected solid was dissolved in a minimum volume of hot methanol. Upon cooling, a dark material deposited. The methanol solution was decanted and diluted to twice its volume with ethyl acetate. A light brown solid deposited after standing for 48 hours. The solid was isolated by filtration, dried, and redissolved in hot methanol (30 mL). The solution was concentrated to 20 mL and diluted with an equal volume of ethyl acetate. On cooling, a tan solid formed. The solid was isolated by filtration and washed with methanol/ethyl acetate to give 25 mg (17%) of the title compound. 1H NMR (DMSO-d6): δ7.42 (s, 2H), 7.82 (d, J=8.5 Hz, 2H), 7.90 (d, J=8.5 Hz, 2H), 8.28 (s, 1H), 8.11 (d, J=6.0 Hz, 1H), 8.38 (d, J=6.0 Hz, 1H), 9.35 (d, J=13.5 Hz, 1H), 11.53 (s, 1H), 11.60 (d, J=13.5 Hz, 1H), 14.6 (br s, 1H); C14H12N4O3S: APCI−MS m/z 315 (M−H).

Workup

  1. temperatureThe reaction mixture was refluxed
  2. temperaturecooled
  3. filtrationfiltered
  4. dissolutionThe collected solid was dissolved in a minimum volume of hot methanol
  5. temperatureUpon cooling
  6. customThe methanol solution was decanted
  7. additiondiluted to twice its volume with ethyl acetate
  8. waitafter standing for 48 hours
  9. customThe solid was isolated by filtration
  10. customdried
  11. dissolutionredissolved in hot methanol (30 mL)
  12. concentrationThe solution was concentrated to 20 mL
  13. additiondiluted with an equal volume of ethyl acetate
  14. temperatureOn cooling
  15. customa tan solid formed
  16. customThe solid was isolated by filtration
  17. washwashed with methanol/ethyl acetate

Sources & evidence

ORD record
ord-4bab44ea1be04f7a8fd217e86b47bc5e
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

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