Hydrochloric Acid → 3-(((2,5-Dimethylphenyl)methyl)amino)benzenesulfonic acid

HRID 1065097Notes

Reaction equation

HRID 1065097 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]=[CH:27][C:26]([CH3:29])=[CH:25][C:22]=1[CH2:23]Cl.Cl>C(#N)C.O>[CH3:20][C:21]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][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 69987Benzene, 2-(chloromethyl)-1,4-dimethyl-HCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 128529313-(((2,5-Dimethylphenyl)methyl)amino)benzenesulfonic acidYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a stirred slurry of 52.0 g (0.30 mole) of 3-aminobenzenesulfonic acid in 225 ml of hot (65° C.) water was added 83.0 g (0.61 mole) of sodium acetate trihydrate and 75 ml of acetonitrile. The temperature was stabilized at approximately 67°-68° C. and a solution of 30.93 g (0.20 mole) of 2,5-dimethylbenzyl chloride in 75 ml of acetonitrile added dropwise over 1 hr. The resulting orange solution was refluxed for 31/2 hrs, then acidified with 40 ml of conc. HCl while simultaneously distilling off 80 ml of acetonitrile. After placing the reaction mixture in a refrigerator a flocculent cream-colored precipitate formed which was collected by vacuum filtration, washed with water and air-dried. The collected solids were then slurried in 400 ml of boiling methanol for 20 minutes, then vacuum filtered and then dried in vacuo at about 60° C., which afforded 30.86 g (53.0% yield) of purified 3-(((2,5-dimethylphenyl)methyl)amino)benzenesulfonic acid as a white powder having a melting point greater than 275° C.

Workup

  1. customwas stabilized at approximately 67°-68° C.
  2. temperatureThe resulting orange solution was refluxed for 31/2 hrs
  3. distillationwhile simultaneously distilling off 80 ml of acetonitrile
  4. customformed which
  5. filtrationwas collected by vacuum filtration
  6. washwashed with water
  7. customair-dried
  8. filtrationvacuum filtered
  9. customdried in vacuo at about 60° C.

Sources & evidence

ORD record
ord-31dd6adca0174e6fb4aa80d062e31663
Source dataset
uspto-grants-1982_05
Patent number
US04328244

Reaction notes

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