HCID 641343, compound → Saccharin

HRID 2057555Notes

Reaction equation

HRID 2057555 reaction equation
Cl[S:2]([C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7](Cl)=[O:8])(=[O:4])=[O:3].O.[NH3:15]>CO>[CH:11]1[CH:10]=[C:6]2[C:7]([NH:15][S:2](=[O:4])(=[O:3])[C:5]2=[CH:13][CH:12]=1)=[O:8]

Participants

4

Reactant 2

HCID 641343HCID 641343, compoundHCID 12896473Azane;hydrate

Product 1

HCID 5143SaccharinYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 20 g amount of the mixture of o-chlorosulfonylbenzoylchloride and dichlorotolylsultone was added dropwise to 40 ml of methanol with stirring at 15°-20° C. and the mixture was stirred and reacted for 1 hour. After the reaction, the reaction mixture was added dropwise to 35 g of 8% ammonia water with stirring at 20°-25° C., and the reaction mixture was kept for one night. Then, methanol was removed by distillation from the reaction mixture under a reduced pressure, and hydrochloric acid was added to the residual product to adjust pH to 1-2. The precipitated crystals were filtered and washed with water and dried, to obtain 14.3 g of white crystals of o-sulfobenzimide having a melting point of 227°-228° C. (yield of 93%).

Workup

  1. stirringthe mixture was stirred
  2. customreacted for 1 hour
  3. customAfter the reaction
  4. stirringwith stirring at 20°-25° C.
  5. waitthe reaction mixture was kept for one night
  6. customThen, methanol was removed by distillation from the reaction mixture under a reduced pressure, and hydrochloric acid
  7. additionwas added to the residual product
  8. filtrationThe precipitated crystals were filtered
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-c39aeb28e5a849b09187ef36db3cea00
Source dataset
uspto-grants-1980_07
Patent number
US04211723

Reaction notes

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