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

HRID 729001

반응식

HRID 729001 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-57fb4903711c4e029181b8fde5791f12
출처 데이터셋
uspto-grants-1991_09
특허 번호
US05051436

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