Реакция #2240

Уравнение реакции

3-phenylisocarbostyril

Sodium hydride

3,4-Dimethoxybenzenesulphonylchloride

→

title compound

Выход 46.7%

N-(3,4-Dimethoxybenzenesulphonyl)-3-phenylisocarbostyril

Выход 46.7%

Растворители

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   workup.STIRRINGwith continued stirring at 0° C. for a further 15 minutes
2. 2
   ТемператураThe reaction mixture was warmed to room temperature
3. 3
   workup.STIRRINGstirred for 24 hours
4. 4
   ДругоеThe DMF was evaporated under high vacuum
5. 5
   Другоеthe residue partitioned between ethyl acetate (2×12 ml) and water (12 ml)
6. 6
   СушкаThe combined organic phases were dried over magnesium sulphate
7. 7
   Концентрированиеconcentrated in vacuo
8. 8
   Другоеto yield a yellow oil
9. 9
   ДругоеPurification
10. 10
    Промывкаeluting with 50% ethyl acetate in hexane
11. 11
    Другоеyielded an oil which
12. 12
    Другоеwas crystallized from ethyl acetate/hexane

Методика

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).

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