Sulfanilamide → HCID 178512579, compound

HRID 1792770Notes

Reaction equation

HRID 1792770 reaction equation
[S:1]([NH2:11])(=[O:10])([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1)=[O:2].C([NH:20][C:21]#[N:22])(=O)C1C=CC=CC=1>C(O)C.Cl>[S:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:21]([NH2:22])=[NH:20])=[CH:7][CH:8]=1)(=[O:10])(=[O:2])[NH2:11]

Participants

5

Reactant 2

HCID 5333SulfanilamideHCID 84805Benzamide, N-cyano-

Product 1

HCID 178512579HCID 178512579, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of sulphanilamide (20 g, 0.166 mol), benzoyl cyanamide (34 g, 0.33 mol) in ethanol (60 ml) and concentrated hydrochloric acid (11 ml) was heated on a steam bath until the solvent had evaporated. Water was added and the mixture heated at reflux for 5 minutes. Sodium hydroxide (14.4 g) was added and the mixture heated at reflux. The mixture was allowed to cool and was adjusted to pH2 with hydrochloric acid and the precipitated solid removed by filtration. The filtrate was neutralised and the solvent removed by evaporation. The residue was recrystallized from water to give the crude title product. m/z: 215 [MH]+.

Workup

  1. temperaturewas heated on a steam bath until the solvent
  2. customhad evaporated
  3. additionWater was added
  4. temperaturethe mixture heated
  5. temperatureat reflux for 5 minutes
  6. additionSodium hydroxide (14.4 g) was added
  7. temperaturethe mixture heated
  8. temperatureat reflux
  9. temperatureto cool
  10. customthe precipitated solid removed by filtration
  11. customthe solvent removed by evaporation
  12. customThe residue was recrystallized from water

Sources & evidence

ORD record
ord-e5c80abd908e434e87362660a829fe62
Source dataset
uspto-grants-2006_07
Patent number
US07078410B2

Reaction notes

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