Hydrochloric Acid → HCID 23675557, compound

HRID 1065090Notes

Reaction equation

HRID 1065090 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].[OH-].[Na+:13].[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18]Cl.Cl>O>[Cl:14][C:15]1[CH:16]=[C:17]([CH2:18][NH:9][C:6]2[CH:5]=[CH:4][C:3]([S:1]([O-:11])(=[O:10])=[O:2])=[CH:8][CH:7]=2)[CH:20]=[CH:21][CH:22]=1.[Na+:13]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8479Sulfanilic acidHCID 12103m,alpha-DichlorotolueneHCID 14798Sodium Hydroxide

Product 1

HCID 23675557HCID 23675557, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of 17.2 g of sulfanilic acid, 100 ml of 5 Normal (N) sodium hydroxide solution, 100 ml of water and 16.1 g of 3-chlorobenzyl chloride was stirred in a 500-ml Erlenmeyer flask and heated to about 40°-50° C. After 5 days, a small portion of the reaction mixture was poured into dilute hydrochloric acid. A white precipitate formed which was insoluble in boiling water. The remaining portion of the reaction mixture was poured over 800 ml of ice-water, acidified with concentrated hydrochloric acid, and then filtered through a sintered glass funnel. After filtering, about 50 ml of slurry remained in the funnel. This slurry was put in a beaker, 200 ml of ethanol was added and the mixture was warmed to about 50° C. A solution of 5N sodium hydroxide was added dropwise until solution was achieved. The solution was carbon treated and filtered. Concentration of the filtrate gave a gummy semisolid which was recrystallized from 200 ml of acetic acid containing a small quantity of water. After vacuum oven drying, 5.4 g of the purified product, sodium 4-(((3-chlorophenyl)methyl)amino)benzenesulfonate, was obtained as an off-white solid having a melting point (mp) greater than 280° C.

Workup

  1. temperatureheated to about 40°-50° C
  2. customA white precipitate formed which
  3. filtrationfiltered through a sintered glass funnel
  4. filtrationAfter filtering
  5. additionwas added
  6. additionA solution of 5N sodium hydroxide was added dropwise until solution
  7. additiontreated
  8. filtrationfiltered
  9. customConcentration of the filtrate gave a gummy semisolid which
  10. customwas recrystallized from 200 ml of acetic acid containing a small quantity of water
  11. customAfter vacuum oven drying

Sources & evidence

ORD record
ord-5e73517dbed84848a2db187b99faabd0
Source dataset
uspto-grants-1982_05
Patent number
US04328244

Reaction notes

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