Hydrochloric Acid → HCID 12852932, compound

HRID 1065098Notes

Reaction equation

HRID 1065098 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+].[CH3:20][C:21]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[C:22]=1[CH2:23]Cl.Cl>O.C(#N)C>[CH3:20][C:21]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[C:22]=1[CH2:23][NH:1][C:2]1[CH:3]=[C:4]([S:8]([OH:11])(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 84743-Aminobenzenesulfonic acidHCID 741082,4,6-Trimethylbenzyl chlorideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 12852932HCID 12852932, compoundYield 40.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×

Procedure

A mixture of 52.0 g (0.30 mole) of 3-aminobenzenesulfonic acid, 83.0 g (0.61 mole) of sodium acetate trihydrate, 33.7 g (0.20 mole) of 2,4,6-trimethylbenzyl chloride, 225 ml of water and 150 ml of acetonitrile was refluxed for 4 hrs, then acidified by the dropwise addition of 40 ml of conc. HCl over 30 minutes during which time approximately 100 ml of acetonitrile was distilled off. The resulting mixture was vacuum filtered while hot (80° C.) and a grayish-white powder obtained which was then slurried in 300 ml of hot (65° C.) water for 20 minutes and vacuum filtered. The slurrying process was repeated with water and then with 300 ml of boiling methanol for 20 minutes. Vacuum filtration followed by drying in vacuo at about 60° C. afforded 24.85 g (40.7% yield) of purified 3-(((2,4,6-trimethylphenyl)methyl)amino)benzenesulfonic acid as a white powder having a melting point greater than 275° C.

Workup

  1. temperaturewas refluxed for 4 hrs
  2. distillationwas distilled off
  3. filtrationfiltered while hot (80° C.)
  4. customa grayish-white powder obtained which
  5. filtrationvacuum filtered
  6. filtrationVacuum filtration
  7. customby drying in vacuo at about 60° C.

Sources & evidence

ORD record
ord-76e3ab5b762c4b8eb9d4fef1a88a17b8
Source dataset
uspto-grants-1982_05
Patent number
US04328244

Reaction notes

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