Sulfanilic acid → HCID 12852926, compound

HRID 1065094Notes

Reaction equation

HRID 1065094 reaction equation
[S:1]([OH:11])(=[O:10])([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1)=[O:2].O.O.O.C([O-])(=O)C.[Na+].Br[CH2:21][C:22]1[CH:35]=[CH:34][C:25]([C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:27])=[CH:24][CH:23]=1>C(#N)C.O.CO>[C:26]([C:25]1[CH:24]=[CH:23][C:22]([CH2:21][NH:9][C:6]2[CH:5]=[CH:4][C:3]([S:1]([OH:11])(=[O:10])=[O:2])=[CH:8][CH:7]=2)=[CH:35][CH:34]=1)(=[O:27])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

7

Reactant 3

HCID 8479Sulfanilic acidHCID 1229514-(Bromomethyl)benzophenoneHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 12852926HCID 12852926, compoundYield 54.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
70 °C

Procedure

To a 1-liter 3-necked round-bottomed flask equipped with overhead stirrer, reflux condenser, dropping funnel and thermometer and containing a stirred slurry of 33.8 g (0.195 mole) of sulfanilic acid in 150 ml of warm (60° C.) water was added 55 g (0.404 mole) of sodium acetate trihydrate and 50 ml of acetonitrile. The resulting yellow solution was heated to 70° C. and a solution of 35 g (0.127 mole) of the 4-(bromomethyl)benzophenone prepared above in 80 ml of acetonitrile was added dropwise over 11/2 hrs. The resulting solution was then refluxed for 5 hrs. Approximately 75 ml of acetonitrile was then removed by distillation at the same time that a dropwise addition of 32 ml of conc. HCl (over a 20 minute period) was made. The mixture was then vacuum filtered at 80° C. which gave a pale yellow powder. The powder was then slurried in 250 ml of water for 15 minutes and again isolated by vacuum filtration. The resulting solids were reslurried in 250 ml of methanol and isolated by vacuum filtration which afforded 25.28 g (54.2%) of purified 4-(((4-benzoylphenyl)methyl)amino)benzenesulfonic acid as a pale yellow powder, which decomposed at 257°-259° C.

Workup

  1. customTo a 1-liter 3-necked round-bottomed flask equipped with overhead stirrer
  2. temperaturereflux condenser
  3. additionwas added dropwise over 11/2 hrs
  4. temperatureThe resulting solution was then refluxed for 5 hrs
  5. customApproximately 75 ml of acetonitrile was then removed by distillation at the same time that a dropwise addition of 32 ml of conc. HCl (over a 20 minute period)
  6. filtrationvacuum filtered at 80° C. which
  7. customgave a pale yellow powder
  8. customagain isolated by vacuum filtration
  9. customisolated by vacuum filtration which

Sources & evidence

ORD record
ord-f53eff30c1b144b6a795b941f72eb50b
Source dataset
uspto-grants-1982_05
Patent number
US04328244

Reaction notes

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