Chlorosulfonic acid → 4-Ethoxy-3-(8-cyclopentyl-6-methyl-4-oxo-3,4-dihydro-imidazol[1,5-a][1,3,5]-triazin-2-yl)-benzenesulfonyl chloride

HRID 392664

Reaction equation

HRID 392664 reaction equation
[CH:1]1([C:6]2[N:7]=[C:8]([CH3:25])[N:9]3[C:14](=[O:15])[NH:13][C:12]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[O:22][CH2:23][CH3:24])=[N:11][C:10]=23)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:26][S:27](O)(=[O:29])=[O:28]>ClCCl>[CH2:23]([O:22][C:17]1[CH:18]=[CH:19][C:20]([S:27]([Cl:26])(=[O:29])=[O:28])=[CH:21][C:16]=1[C:12]1[NH:13][C:14](=[O:15])[N:9]2[C:8]([CH3:25])=[N:7][C:6]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[C:10]2[N:11]=1)[CH3:24]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 1357235138-Cyclopentyl-2-(2-ethoxy-phenyl)-6-methyl-3H-imidazo[1,5-a][1,3,5]triazin-4-one

Product 1

HCID 1357235154-Ethoxy-3-(8-cyclopentyl-6-methyl-4-oxo-3,4-dihydro-imidazol[1,5-a][1,3,5]-triazin-2-yl)-benzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

372.3 mg (1.1 mmol) of 8-cyclopentyl-2-(2-ethoxy-phenyl)-6-methyl-3H-imidazo [1,5-α][1,3,5]triazin-4-one (example IX) are added in portions to 0.66 ml (9.9 mmol) of ice-cooled chlorosulfonic acid. The mixture is subsequently stirred overnight at room temperature before being diluted with dichloromethane and poured onto ice water. The organic phase is separated off. The aqueous phase is extracted once again with dichloromethane and the organic phases are combined, dried and evaporated.

Workup

  1. additionpoured onto ice water
  2. customThe organic phase is separated off
  3. extractionThe aqueous phase is extracted once again with dichloromethane
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-ebcff7ab3b3541c0bb52e5b6911c5da6
Source dataset
uspto-grants-2004_10
Patent number
US06803365B2

Linked notes

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