Triethylamine → 2-(4-(S-Methyl-N-(methylsulfonyl)sulfonimidoyl)benzyl)isoindoline-1,3-dione

HRID 527358Notes

Reaction equation

HRID 527358 reaction equation
[CH3:1][S:2]([C:5]1[CH:22]=[CH:21][C:8]([CH2:9][N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])=[CH:7][CH:6]=1)(=[NH:4])=[O:3].C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>ClCCl>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])=[CH:21][CH:22]=1)(=[N:4][S:31]([CH3:30])(=[O:33])=[O:32])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 867116292-(4-(S-Methylsulfonimidoyl)benzyl)isoindoline-1,3-dione

Product 1

HCID 867116282-(4-(S-Methyl-N-(methylsulfonyl)sulfonimidoyl)benzyl)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(4-(S-methylsulfonimidoyl)benzyl)isoindoline-1,3-dione (preparation 17b, 2.50 g, 7.95 mmol) and triethylamine (2.2 mL, 16 mmol) in dichloromethane (20 mL) is cooled at 0° C. and treated with methanesulfonyl chloride (620 μL, 8.0 mmol). The mixture is stirred at this temperature for 1.5 h and then washed with water. The organic layer is concentrated under reduced pressure, and the residue is suspended in a mixture of methanol and water. The precipitate is filtered, washed with water, and dried. Yield: 273 mg (8% of theory); ESI mass spectrum: [M+H]+=393, r.t. HPLC: 0.44 min (X012_S01).

Workup

  1. washwashed with water
  2. concentrationThe organic layer is concentrated under reduced pressure
  3. additionthe residue is suspended in a mixture of methanol and water
  4. filtrationThe precipitate is filtered
  5. washwashed with water
  6. customdried
  7. custom=393, r.t
  8. custom0.44 min (X012_S01)

Sources & evidence

ORD record
ord-64095652589442a28667ef95c9615ec7
Source dataset
uspto-grants-2016_05
Patent number
US09346794B1

Reaction notes

Loading…