Chlorosulfonic acid → HCID 135533285, compound

HRID 1016350Notes

Reaction equation

HRID 1016350 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[NH:15][C:14](=[O:16])[C:13]2=[C:17]([CH3:25])[N:18]=[C:19]([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[N:12]2[N:11]=1)[CH3:2].[S:26]([Cl:30])(=O)(=[O:28])[OH:27]>>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([S:26]([Cl:30])(=[O:28])=[O:27])=[CH:6][C:5]=1[C:10]1[NH:15][C:14](=[O:16])[C:13]2=[C:17]([CH3:25])[N:18]=[C:19]([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[N:12]2[N:11]=1)[CH3:2]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 1356049597-Cyclopentyl-2-(2-ethoxy-phenyl)-5-methyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one

Product 1

HCID 135533285HCID 135533285, compound

Procedure

At 0° C., 7.0 g (20.7 mmol) of 2-(2-ethoxyphenyl)-5-methyl-7-cyclopentyl-3H-imidazo[5,1-f][1,2,4]-triazin-4-one (Example 15A) are added carefully to 24.1 g (207 mmol) of chlorosulphuric acid. The mixture is allowed to warm to room temperature and stirred overnight. The solution is carefully added to 200 ml of ice-water and extracted twice with dichloromethane. The combined organic phases are dried over sodium sulphate and the solvent is distilled off under reduced pressure. The sulphonyl chloride is dried under reduced pressure and reacted further to the sulphonamides without further purification.

Workup

  1. extractionextracted twice with dichloromethane
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. distillationthe solvent is distilled off under reduced pressure
  4. dry with materialThe sulphonyl chloride is dried under reduced pressure
  5. customreacted further to the sulphonamides without further purification

Sources & evidence

ORD record
ord-0ec0ffbba9a94c80933efa7eeb5c8f88
Source dataset
uspto-grants-2002_11
Patent number
US06476029B1

Reaction notes

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