Water → 5-Cyclohexyl Saccharin

HRID 34886Notes

Reaction equation

HRID 34886 reaction equation
C([S:5]([NH:8][C:9]1C=C[C:15]([CH:18]2CCCCC2)=[CH:14][C:10]=1[C:11](O)=O)(=[O:7])=[O:6])(C)(C)C.O.C1(C)C(S(O)(=O)=[O:32])=CC=CC=1.O.[C:37]1([CH3:43])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[CH:37]1([C:43]2[CH:11]=[C:10]3[C:14](=[CH:15][CH:18]=2)[S:5](=[O:7])(=[O:6])[NH:8][C:9]3=[O:32])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

5

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 124969952-Methylbenzenesulfonic acid hydrateHCID 212970242-(t-Butylsulfonamido)-5-Cyclohexylbenzoic Acid

Product 1

HCID 142051375-Cyclohexyl Saccharin

Procedure

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.

Workup

  1. customequipped with a Dean-Strark trap
  2. temperaturethe reaction mixture is warmed to reflux
  3. concentrationconcentrated
  4. customa rotary evaporator
  5. dissolutionThe resulting crude semi-solid oil is dissolved in a minimum amount of ethyl acetate at the boiling point
  6. additionby the addition of hexane
  7. customThe desired cyclohexyl saccharin compound crystallizes
  8. temperatureon cooling
  9. dissolutionThe dissolution and crystallization procedure
  10. customnmr delta=1-2.2 m cyclohexyl, delta=6.2 s broad N--H, delta=7-8 m

Sources & evidence

ORD record
ord-9a707e8d9ccc47dc9395d604584e4745
Source dataset
uspto-grants-1988_08
Patent number
US04764239

Reaction notes

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