Saccharin → N-(phenylsulfonyl)-benzo-1,2,3-thiadiazole-7-carboxylic acid amide

HRID 729001Notes

Reaction equation

HRID 729001 reaction equation
[Na].[S:2]1([C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:6](=[O:7])[NH:5]1)(=[O:4])=[O:3].[S:14]1[C:18]2[C:19](C(Cl)=O)=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[N:15]1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:13]1([S:2]([NH:5][C:6]([C:19]2[C:18]3[S:14][N:15]=[N:16][C:17]=3[CH:22]=[CH:21][CH:20]=2)=[O:7])(=[O:3])=[O:4])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 5143SaccharinHCID 5360545SodiumHCID 183776071,2,3-Benzothiadiazole-7-carbonyl chloride

Product 1

HCID 54415936N-(phenylsulfonyl)-benzo-1,2,3-thiadiazole-7-carboxylic acid amide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

After the addition of a spatula tip of 4-dimethylaminopyridine to a suspension of 4 g of the sodium salt of saccharin in 60 ml of methylene chloride, a solution of 3.9 g of benzo-1,2,3-thiadiazole-7-carboxylic acidchloride in 20 ml of methylene chloride is added dropwise at a maximum of 20° C. The mixture is stirred overnight at room temperature and thenext day the suspension is poured onto ice-water and extracted with ethyl acetate. The extracts are washed with dilute sodium hydrogen carbonate solution and water, dried and concentrated by evaporation. The residue is recrystallised from tetrahydrofuran/hexane to yield the title compound having a melting point of 173°-175° C.

Workup

  1. additionis poured onto ice-water
  2. extractionextracted with ethyl acetate
  3. washThe extracts are washed with dilute sodium hydrogen carbonate solution and water
  4. customdried
  5. concentrationconcentrated by evaporation
  6. customThe residue is recrystallised from tetrahydrofuran/hexane

Sources & evidence

ORD record
ord-57fb4903711c4e029181b8fde5791f12
Source dataset
uspto-grants-1991_09
Patent number
US05051436

Reaction notes

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