Hydrochloric Acid → HCID 23675555, compound

HRID 1065091Notes

Reaction equation

HRID 1065091 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].[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1.Cl>O>[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][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:17][CH:16]=1.[Na+:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8479Sulfanilic acidHCID 96024-Fluorobenzyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 23675555HCID 23675555, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 17.3 g (0.1 mole) of sulfanilic acid, 100 ml of 5N sodium hydroxide solution and 100 ml of water was added 14.4 g (0.1 mole) of 4-fluorobenzyl chloride which was then mixed and heated to about 45°-55° C. in a 500-ml Erlenmeyer flask for 48 hours. After heating, the reaction mixture was poured over approximately 1 liter of cold water and acidified with concentrated hydrochloric acid. The resulting slurry was slowly filtered through a fine sintered glass funnel and a top clear yellow solution which did not pass through the filter was decanted away and discarded. The remaining off-white solid was mixed with 100 ml of ethanol and aqueous NaOH solution was added slowly until solution was achieved. The solution was then carbon treated, filtered and concentrated under reduced pressure to obtain 9.0 g of the crude product. Recrystallization from 80 ml of glacial acetic acid, followed by vacuum oven drying gave 2.4 g of the purified product, sodium 4-(((4-fluorophenyl)methyl)amino)benzenesulfonate, as white crystals which decomposed at 275° C.

Workup

  1. additionwas then mixed
  2. temperatureheated to about 45°-55° C. in a 500-ml Erlenmeyer flask for 48 hours
  3. temperatureAfter heating
  4. filtrationThe resulting slurry was slowly filtered through a fine sintered glass funnel
  5. customwas decanted away
  6. additionThe remaining off-white solid was mixed with 100 ml of ethanol and aqueous NaOH solution
  7. additionwas added slowly until solution
  8. additioncarbon treated
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto obtain 9.0 g of the crude product
  12. customRecrystallization from 80 ml of glacial acetic acid
  13. customdrying

Sources & evidence

ORD record
ord-8d8415ef8ce04605a1064b222c2a6df9
Source dataset
uspto-grants-1982_05
Patent number
US04328244

Reaction notes

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