Hydrochloric Acid → HCID 12852930, compound

HRID 1065096Notes

Reaction equation

HRID 1065096 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:8]([OH:11])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.O.O.O.C([O-])(=O)C.[Na+].[N+:20]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=1)([O-:22])=[O:21].Cl>C(#N)C.O>[N+:20]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH:1][C:2]2[CH:3]=[C:4]([S:8]([OH:11])(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=2)=[CH:25][CH:24]=1)([O-:22])=[O:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 84743-Aminobenzenesulfonic acidHCID 660114-Nitrobenzyl bromideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 12852930HCID 12852930, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×

Procedure

After 52.0 g (0.30 mole) of 3-aminobenzenesulfonic acid in 225 ml of warm (65° C.) water and 83.0 (0.61 mole) of sodium acetate trihydrate in 75 ml of acetonitrile was combined and the temperature stabilized at approximately 68°-70° C., 43.2 g (0.20 mole) of 4-nitrobenzyl bromide in 85 ml of warmed acetonitrile was added dropwise over 70 minutes. The orange-red solution was then refluxed for 2 hrs, then acidified with 42 ml of conc. HCl over 40 minutes while simultaneously distilling off 110 ml of acetonitrile. The mixture was filtered hot (70° C.) which gave a light yellow powder. The powder was slurried in 275 ml of hot (75° C.) water for 20 minutes and then filtered. The slurrying process was repeated with water and then with methanol which gave a cream-colored powder. The cream-colored powder was dried in vacuo overnight at 50° C. to afford 35.33 g (57.3% yield) of purified 3-(((4-nitrophenyl)methyl)amino)benzenesulfonic acid as a cream-colored powder having a melting point greater than 275° C.

Workup

  1. customstabilized at approximately 68°-70° C.
  2. temperatureThe orange-red solution was then refluxed for 2 hrs
  3. distillationwhile simultaneously distilling off 110 ml of acetonitrile
  4. filtrationThe mixture was filtered hot (70° C.) which
  5. customgave a light yellow powder
  6. filtrationfiltered
  7. customwith methanol which gave a cream-colored powder
  8. customThe cream-colored powder was dried in vacuo overnight at 50° C.

Sources & evidence

ORD record
ord-1188ee97c79e4c4e803150d19339e329
Source dataset
uspto-grants-1982_05
Patent number
US04328244

Reaction notes

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