Hydrochloric Acid → HCID 12852929, compound

HRID 1065095Notes

Reaction equation

HRID 1065095 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+].[F:20][C:21]([F:31])([F:30])[C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25]Cl.Cl>O.C(#N)C>[F:20][C:21]([F:30])([F:31])[C:22]1[CH:23]=[C:24]([CH2:25][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:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 84743-Aminobenzenesulfonic acidHCID 697163-(Trifluoromethyl)benzyl chlorideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 12852929HCID 12852929, compoundYield 23.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
60 °C

Procedure

To 52.0 g (0.30 mole) of 3-aminobenzenesulfonic acid in 225 ml of water was added 83.0 g (0.61 mole) of sodium acetate trihydrate and 75 ml of acetonitrile. The solution was stabilized at about 70° C. and a solution of 38.92 g (0.20mole) of 3-(trifluoromethyl)benzyl chloride in 75 ml of acetonitrile was added dropwise. The resulting orange solution was refluxed for 4 hrs, then acidified by the dropwise addition of 42 ml of conc. HCl while simultaneously removing 105 ml of acetonitrile by distillation. After standing overnight, a flocculent cream-colored solid crystalized which was removed by vacuum filtration. The collected solids were then slurried in 300 ml of warm (60° C.) water for 20 minutes and then filtered. The slurrying process was repeated using 300 ml of boiling methanol and the solids isolated by vacuum filtration. Air-drying in vacuo at about 60° C. gave 15.4 g (23.2% yield) of purified 3-(((3-(trifluoromethyl)phenyl)methyl)amino)benzenesulfonic acid as a white powder having a melting point greater than 275° C.

Workup

  1. customwas stabilized at about 70° C.
  2. temperatureThe resulting orange solution was refluxed for 4 hrs
  3. customwhile simultaneously removing 105 ml of acetonitrile
  4. distillationby distillation
  5. customa flocculent cream-colored solid crystalized which
  6. customwas removed by vacuum filtration
  7. filtrationfiltered
  8. customthe solids isolated by vacuum filtration
  9. customAir-drying in vacuo at about 60° C.

Sources & evidence

ORD record
ord-8ca21feadb1d487491cdcc826a4a8635
Source dataset
uspto-grants-1982_05
Patent number
US04328244

Reaction notes

Loading…