Hydrochloric Acid → N-[4-(2-aminoethyl)phenyl]Benzenesulfonamide

HRID 1977458Notes

Reaction equation

HRID 1977458 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1.Cl.O.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCOCC1.N1C=CC=CC=1>[NH2:2][CH2:3][CH2:4][C:5]1[CH:11]=[CH:10][C:8]([NH:9][S:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:22])=[O:21])=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 219979234-(2-Aminoethyl)aniline hydrochloride

Product 1

HCID 15281645N-[4-(2-aminoethyl)phenyl]Benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-(2-aminoethyl)aniline hydrochloride salt (10.0 g, 78 mmol) was dissolved in dioxane (200 mL) followed by the addition of 5 M HCl (14.6 ml) and water (25 ml). The solution was cooled in an ice bath and was treated quickly with benzenesulfonyl chloride (10.3 ml, 81 mmol). Pyridine (10 ml) was added and the solution stirred at ambient temperature for 16 h. The solvent was removed under reduced pressure and the residue was dissolved in water (300 ml) and washed with 3 portions of diethylether. The aqueous solution was treated with 80 ml of 5 N sodium hydroxide and was washed again with 3 portions of diethylether. The aqueous phase was adjusted to a pH of approximately 9 by the addition of 40 ml of 5N HCl. The solids were collected and dried. NMR, MS, EA.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in water (300 ml)
  4. washwashed with 3 portions of diethylether
  5. additionThe aqueous solution was treated with 80 ml of 5 N sodium hydroxide
  6. washwas washed again with 3 portions of diethylether
  7. additionThe aqueous phase was adjusted to a pH of approximately 9 by the addition of 40 ml of 5N HCl
  8. customThe solids were collected
  9. customdried

Sources & evidence

ORD record
ord-1497363f54184f71a7e477dfff968256
Source dataset
uspto-grants-2001_05
Patent number
US06232337B1

Reaction notes

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