Potassium Carbonate → HCID 73296091, compound

HRID 2172662Notes

Reaction equation

HRID 2172662 reaction equation
[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:5]=2[S:4](=[O:15])(=[O:14])[NH:3]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][N:27]1[C:36](=[O:37])[C:35]2[CH:38]=[CH:39][CH:40]=[C:33]3[C:34]=2[C:29](=[CH:30][CH:31]=[CH:32]3)[C:28]1=[O:41]>CN(C=O)C>[O:41]=[C:28]1[C:29]2[C:34]3[C:33](=[CH:40][CH:39]=[CH:38][C:35]=3[C:36](=[O:37])[N:27]1[CH2:26][CH2:25][CH2:24][CH2:23][N:3]1[C:2](=[O:1])[C:6]3[CH:7]=[CH:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:5]=3[S:4]1(=[O:15])=[O:14])[CH:32]=[CH:31][CH:30]=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 353793NSC602923HCID 27823602-(4-bromobutyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Product 1

HCID 73296091HCID 73296091, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 3-oxo-2,3-dihydrobenzo[d]isothiazole-6-carboxylic acid 1,1-dioxide (8) (1 mmol) and anhydrous K2CO3 (5 mmol) in DMF was added 2-(4-bromobutyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (3b) (3 mmol). The reaction mixture was gently refluxed for overnight, cooled to room temperature and poured into the crushed ice. The resulted solution was acidified with con. HCl and extracted with ethylacetate. The organic layer was washed with water, dried over anhydrous Na2SO4 and concentrated under vacuum to get the crude product. The Crude residue was purified by flash column chromatography using MeOH—CHCl3 (2:8) to obtain the desired product. 1H NMR (400 MHz, DMSO-d6) δ 8.54-8.34 (m, 6H), 7.91-7.77 (m, 3H), 4.41-4.37 (m, 2H), 4.14-4.08 (m, 2H), 1.89-1.71 (m, 4H). MS (ES−) m/z 477 (M−H)−.

Workup

  1. temperatureThe reaction mixture was gently refluxed for overnight
  2. extractionHCl and extracted with ethylacetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under vacuum
  6. customto get the crude product
  7. customThe Crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-43c999e2f5a34b3ebc47be0134fdc294
Source dataset
uspto-grants-2015_06
Patent number
US09056835B2

Reaction notes

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