Phosphorus pentachloride → 5-ethyl-furo[3,2-d]isothiazole-3(2H)-one-1,1-dioxide

HRID 1388189Notes

Reaction equation

HRID 1388189 reaction equation
[CH2:1]([C:3]1[O:7][C:6]([S:8](=[O:11])(=[O:10])[NH2:9])=[C:5]([C:12]([OH:14])=O)[CH:4]=1)[CH3:2].P(Cl)(Cl)(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[O:7][C:6]2[S:8](=[O:11])(=[O:10])[NH:9][C:12](=[O:14])[C:5]=2[CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 20471868HCID 20471868, compound

Product 1

HCID 204718665-ethyl-furo[3,2-d]isothiazole-3(2H)-one-1,1-dioxideYield 46%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5.0 gm (0.023 mol) of 5-ethyl-2-sulfamoyl-furan-3-carboxylic acid were admixed with 4.75 gm (0.023 mol of phosphorus pentachloride in 300 ml of anhydrous toluene, and the mixture was refluxed for 8 hours. After filtering, the filtrate was evaporated in vacuo and the residue was recrystallized from carbon tetrachloride, yielding 2.1 gm (46% of theory) of 5-ethyl-furo[3,2-d]isothiazole-3(2H)-one-1,1-dioxide.

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. filtrationAfter filtering
  3. customthe filtrate was evaporated in vacuo
  4. customthe residue was recrystallized from carbon tetrachloride

Sources & evidence

ORD record
ord-293d83ea77e34f1c9e2b4e2b2efbc759
Source dataset
uspto-grants-1984_02
Patent number
US04430355

Reaction notes

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