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

HRID 729000

Reaction equation

HRID 729000 reaction equation
[C:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[S:17]1[C:21]2[C:22]([C:26](Cl)=[O:27])=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[N:18]1.Cl>C(Cl)Cl>[C:1]1([S:7]([NH:10][C:26]([C:22]2[C:21]3[S:17][N:18]=[N:19][C:20]=3[CH:25]=[CH:24][CH:23]=2)=[O:27])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7370BenzenesulfonamideHCID 183776071,2,3-Benzothiadiazole-7-carbonyl chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.2 g of benzenesulfonamide are introduced at from 0°-5° C. into 50 ml of abs. pyridine and, while stirring at that temperature, a solution of 3.9 g of benzo-1,2,3-thiadiazole-7-carboxylic acid chloride in20 ml of methylene chloride is added dropwise. The mixture is stirred overnight and then poured onto ice-water, rendered slightly acidic with hydrochloric acid and extracted with methylene chloride, and the extracts are washed with water, dried and concentrated by evaporation. The residue is dissolved warm in tetrahydrofuran, treated with some silica gel, filtered, concentrated by evaporation and then recrystallised from tetrahydrofuran/hexane. The title compound resulting melts at 231°-233° C.

Workup

  1. additionpoured onto ice-water
  2. extractionextracted with methylene chloride
  3. washthe extracts are washed with water
  4. customdried
  5. concentrationconcentrated by evaporation
  6. dissolutionThe residue is dissolved
  7. temperaturewarm in tetrahydrofuran
  8. additiontreated with some silica gel
  9. filtrationfiltered
  10. concentrationconcentrated by evaporation
  11. customrecrystallised from tetrahydrofuran/hexane

Sources & evidence

ORD record
ord-4fd4ff4754b84b008f3ee20d61297533
Source dataset
uspto-grants-1991_09
Patent number
US05051436

Linked notes

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