Chlorosulfonic acid → 4-Ethoxy-3-(6-methyl-4-oxo-8-propyl-3,4-dihydro-imidazo[1,5-a][1,3,5]triazin-2-yl)-benzene-sulfonyl chloride

HRID 8621

Reaction equation

HRID 8621 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])[N:13]2[C:17]([CH3:23])=[N:18][C:19]([CH2:20][CH2:21][CH3:22])=[C:12]2[N:11]=1)[CH3:2].[Cl:24][S:25](O)(=[O:27])=[O:26]>ClCCl>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([S:25]([Cl:24])(=[O:27])=[O:26])=[CH:6][C:5]=1[C:10]1[NH:15][C:14](=[O:16])[N:13]2[C:17]([CH3:23])=[N:18][C:19]([CH2:20][CH2:21][CH3:22])=[C:12]2[N:11]=1)[CH3:2]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 1354758792-(2-ethoxyphenyl)-6-methyl-8-propyl-3H-imidazo[1,5-a][1,3,5]triazin-4-one

Product 1

HCID 1354246684-Ethoxy-3-(6-methyl-4-oxo-8-propyl-3,4-dihydro-imidazo[1,5-a][1,3,5]triazin-2-yl)-benzene-sulfonyl chlorideYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.64 g (5.25 mmol) of 2-(2-ethoxyphenyl)-6-methyl-8-propyl-3H-imidazo[1,5-a][1,3,5]triazin-4-one (example VI) are added in portions to 3.14 ml of chlorosulfonic acid while cooling with ice. The reaction mixture is stirred at room temperature for 16 hours, then diluted with dichloromethane and poured onto ice water. The organic phase is washed with water and dried over magnesium sulfate and the solvent is removed in vacuo. 2.15 g (99%) of 4-ethoxy-3-(6-methyl-4-oxo-8-propyl-3,4-dihydro-imidazo[1,5-a][1,3,5]triazin-2-yl)-benzene-sulfonyl chloride are obtained.

Workup

  1. temperaturewhile cooling with ice
  2. additionpoured onto ice water
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-b0655c26605e4b4cb0926cd201146d73
Source dataset
uspto-grants-2006_08
Patent number
US07091203B2

Linked notes

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