تفاعل #63164

معادلة التفاعل

sulfonamido benzoic acid

2-(t-Butylsulfonamido)-5-Cyclohexylbenzoic Acid

toluene

Toluenesulfonic acid monohydrate

water

→

5-Cyclohexyl Saccharin

ظروف التفاعل

المعالجة

1. 1
   أخرىequipped with a Dean-Strark trap
2. 2
   درجة الحرارةthe reaction mixture is warmed to reflux
3. 3
   تركيزconcentrated
4. 4
   أخرىa rotary evaporator
5. 5
   workup.DISSOLUTIONThe resulting crude semi-solid oil is dissolved in a minimum amount of ethyl acetate at the boiling point
6. 6
   workup.ADDITIONby the addition of hexane
7. 7
   أخرىThe desired cyclohexyl saccharin compound crystallizes
8. 8
   درجة الحرارةon cooling
9. 9
   workup.DISSOLUTIONThe dissolution and crystallization procedure
10. 10
    أخرىnmr delta=1-2.2 m cyclohexyl, delta=6.2 s broad N--H, delta=7-8 m

الإجراء التجريبي

The sulfonamido benzoic acid obtained from Example IV is stirred in toluene under argon atmosphere in a flask equipped with a Dean-Strark trap. Toluenesulfonic acid monohydrate (5 mol%) is added and the reaction mixture is warmed to reflux. When no further co-distillation of water is observed, the reaction mixture is cooled to room temperature and concentrated using a rotary evaporator. The resulting crude semi-solid oil is dissolved in a minimum amount of ethyl acetate at the boiling point and the resulting solution then is made cloudy by the addition of hexane. The desired cyclohexyl saccharin compound crystallizes on cooling. The dissolution and crystallization procedure may be repeated if higher purity material is desired. Spectral data for the crystallized product (IR, C=O 1720 cm-1 ; nmr delta=1-2.2 m cyclohexyl, delta=6.2 s broad N--H, delta=7-8 m aromatic) are consistent with the anticipated structure of 5-cyclohexyl saccharin.

المصدر