Sulfuric Acid → 4-Benzylaminesulfonic acid

HRID 965185Notes

Reaction equation

HRID 965185 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:9](=O)(=[O:12])([OH:11])[OH:10]>>[S:9]([C:5]1[CH:6]=[CH:7][C:2]([CH2:1][NH2:8])=[CH:3][CH:4]=1)([OH:12])(=[O:11])=[O:10]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 7504Benzylamine

Product 1

HCID 1889624-Benzylaminesulfonic acidYield 40%

Procedure

p-Sulfobenzylamine was synthesized in 40% yield from benzylamine and fuming sulfuric acid, by an adaptation of the method described in Jacobson et al., J. Med. Chem., 35, 4143-4149 (1992), and was recrystallized from a solution in ammonium hydroxide, upon neutralization with hydrochloric acid. NMR DMSO, d6 δ8.10 (br.s, 3H, NH3+), 7.62 (d, J=8.1 Hz, 2H, o- to sulfo), 7.38 (d, J=8.1 Hz, 2H, m- to sulfo), 4.02 (s, 2H, CH2).

Workup

  1. custom, 35, 4143-4149 (1992), and was recrystallized from a solution in ammonium hydroxide, upon neutralization with hydrochloric acid

Sources & evidence

ORD record
ord-735004ab0f0a4fafb4251a2a9e984a9e
Source dataset
uspto-grants-1998_06
Patent number
US05773423

Reaction notes

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