Sodium hydride → HCID 44322618, compound

HRID 2144Notes

Reaction equation

HRID 2144 reaction equation
[C:1]1([C:7]2[NH:8][C:9]([C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([S:30](Cl)(=[O:32])=[O:31])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]>CN(C)C=O>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([S:30]([N:8]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:9]2=[O:10])(=[O:31])=[O:32])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 27528701(2H)-Isoquinolinone, 3-phenyl-

Product 1

HCID 44322618HCID 44322618, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-phenylisocarbostyril (0.1 g) in N,N-dimethylformamide (2 ml) was cooled to 0° C. under an inert atmosphere. Sodium hydride (0.019 g) was added and the resulting mixture stirred at 0° C. for 5 minutes. 3,4-Dimethoxybenzenesulphonylchloride (0.107 g) was added over a 3 minute period, with continued stirring at 0° C. for a further 15 minutes. The reaction mixture was warmed to room temperature and stirred for 24 hours. The DMF was evaporated under high vacuum and the residue partitioned between ethyl acetate (2×12 ml) and water (12 ml). The combined organic phases were dried over magnesium sulphate and concentrated in vacuo to yield a yellow oil. Purification using column chromatography eluting with 50% ethyl acetate in hexane yielded an oil which was crystallized from ethyl acetate/hexane to furnish the title compound as white crystals (0.089 g).

Workup

  1. stirringwith continued stirring at 0° C. for a further 15 minutes
  2. temperatureThe reaction mixture was warmed to room temperature
  3. stirringstirred for 24 hours
  4. customThe DMF was evaporated under high vacuum
  5. customthe residue partitioned between ethyl acetate (2×12 ml) and water (12 ml)
  6. dry with materialThe combined organic phases were dried over magnesium sulphate
  7. concentrationconcentrated in vacuo
  8. customto yield a yellow oil
  9. customPurification
  10. washeluting with 50% ethyl acetate in hexane
  11. customyielded an oil which
  12. customwas crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-1251e1d4efb04be2a0db094b4b863a07
Source dataset
uspto-grants-1998_03
Patent number
US05728712

Reaction notes

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