Chlorosulfonic acid → HCID 20572195, compound

HRID 1577301Notes

Reaction equation

HRID 1577301 reaction equation
N[C:2]1[CH:7]=[C:6](NCCCC2C=CC=CC=2)[CH:5]=[C:4](N)[N+:3]=1[O-:19].Cl[S:21]([OH:24])(=[O:23])=[O:22].C(N(C(C)C)CC)(C)C>C(Cl)(Cl)Cl>[OH-:19].[S:21]([O:19][N+:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1)([OH:24])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 24638Chlorosulfonic acidHCID 81531DiisopropylethylamineHCID 178507896HCID 178507896, compound

Product 1

HCID 20572195HCID 20572195, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1.00 grams of 2,6-diamino-4-((3-phenyl-1-propyl)amino)-pyridine-1-oxide, 1.50 grams of chlorosulfonic acid, and 2.5 grams of di-isopropylethylamine in 25 ml of chloroform is stirred overnight. The mixture is concentrated in vacuo. The residue is stirred with aqueous sodium bicarbonate, filtered and washed with ether to give the crude product. This is recrystallized from DMF and ethyl acetate to yield the purified 2,6-diamino-4-((3-phenyl)-1-propyl)amino)-1-(sulfooxy)-pyridinium hydroxide, inner salt.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. stirringThe residue is stirred with aqueous sodium bicarbonate
  3. filtrationfiltered
  4. washwashed with ether
  5. customto give the crude product
  6. customThis is recrystallized from DMF and ethyl acetate

Sources & evidence

ORD record
ord-5972299d1ceb444e84a00ef2800d207e
Source dataset
uspto-grants-1981_09
Patent number
US04287338

Reaction notes

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