Chlorosulfonic acid → HCID 178527428, compound

HRID 1277726Notes

Reaction equation

HRID 1277726 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([S:10]([OH:13])(=O)=[O:11])[C:4]=2[N:3]=[N:2]1.[Cl:14]S(O)(=O)=O>>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([S:10]([Cl:14])(=[O:13])=[O:11])[C:4]=2[N:3]=[N:2]1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 178527605HCID 178527605, compound

Product 1

HCID 178527428HCID 178527428, compound

Procedure

Benzotriazole-4-sulphonic acid (5 g, 23 mM) was added, in portions, to chlorosulphonic acid (50 ml), whilst keeping the temperature of the acid below 0°. The resulting solution was heated at 120° overnight, cooled and carefully poured onto ice (1000 g). The solid which formed was collected by filtration, washed well with water and dried in vacuo. This material was dissolved in boiling ethyl acetate and decolorized using a small quantity of charcoal. The product crystallized from the ethyl acetate solution after petroleum ether (40° to 60°) was added, as a white solid (3.94 g, 72 percent), m.p. 173° to 175° (uncorr).

Workup

  1. customthe temperature of the acid below 0°
  2. temperatureThe resulting solution was heated at 120° overnight
  3. temperaturecooled
  4. additioncarefully poured onto ice (1000 g)
  5. customThe solid which formed
  6. filtrationwas collected by filtration
  7. washwashed well with water
  8. customdried in vacuo
  9. dissolutionThis material was dissolved
  10. customThe product crystallized from the ethyl acetate solution after petroleum ether (40° to 60°)
  11. additionwas added, as a white solid (3.94 g, 72 percent), m.p. 173° to 175° (uncorr)

Sources & evidence

ORD record
ord-2711a1fa36f448c89eeadbe6ea0dd4b9
Source dataset
uspto-grants-1981_07
Patent number
US04278748

Reaction notes

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