تفاعل #2240

معادلة التفاعل

3-phenylisocarbostyril

Sodium hydride

3,4-Dimethoxybenzenesulphonylchloride

→

title compound

المردود 46.7%

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

المردود 46.7%

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGwith continued stirring at 0° C. for a further 15 minutes
2. 2
   درجة الحرارةThe reaction mixture was warmed to room temperature
3. 3
   workup.STIRRINGstirred for 24 hours
4. 4
   أخرىThe DMF was evaporated under high vacuum
5. 5
   أخرىthe residue partitioned between ethyl acetate (2×12 ml) and water (12 ml)
6. 6
   تجفيفThe combined organic phases were dried over magnesium sulphate
7. 7
   تركيزconcentrated in vacuo
8. 8
   أخرىto yield a yellow oil
9. 9
   أخرىPurification
10. 10
    غسيلeluting with 50% ethyl acetate in hexane
11. 11
    أخرىyielded an oil which
12. 12
    أخرىwas crystallized from ethyl acetate/hexane

الإجراء التجريبي

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).

المصدر