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

HRID 729001

反応式

HRID 729001 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-57fb4903711c4e029181b8fde5791f12
出典データセット
uspto-grants-1991_09
特許番号
US05051436

関連ノート

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