Hydrochloric Acid → 2H-1,3-Benzodioxole-5-sulfonamide

HRID 1180653Notes

Reaction equation

HRID 1180653 reaction equation
[S:1](Cl)(Cl)(=[O:3])=[O:2].C[N:7](C=O)C.[O:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][CH2:12]1.Cl>O.C(Cl)(Cl)Cl>[O:11]1[C:15]2[CH:16]=[CH:17][C:18]([S:1]([NH2:7])(=[O:3])=[O:2])=[CH:19][C:14]=2[O:13][CH2:12]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 92291,3-BenzodioxoleHCID 24648Sulfuryl chloride

Product 1

HCID 1928092H-1,3-Benzodioxole-5-sulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

Sulfuryl chloride (0.18 mol; 24.3 g) is added dropwise to cooled DMF (0.18 mol; 13.14 g) at a rate to maintain <10° C. The reaction complex is stirred at <10° C. for 30 min. 1,3-Benzodioxole is added dropwise over a period of 10 min. The reaction is then warmed to 80° C. and held for 10 min, and finally warmed to 110° C. and held for 10 min. During heating, the reaction turns brown and HCl evolution is observed. The reaction is cooled to room temperature and left overnight under nitrogen. Next, the reaction is poured onto ice (˜150 g), chloroform (70 mL) and water (70 mL). The organic layer is collected and dripped into concentrated ammonium hydroxide (70 mL), yielding a precipitate, which is collected by filtration, washed with water and dried in vacuo at 40° C. to produce 10.28 g of benzo(1,3)dioxole-5-sulfonamide.

Workup

  1. temperatureto maintain <10° C
  2. waitheld for 10 min
  3. temperaturefinally warmed to 110° C.
  4. waitheld for 10 min
  5. temperatureDuring heating
  6. temperatureThe reaction is cooled to room temperature
  7. waitleft overnight under nitrogen
  8. customThe organic layer is collected
  9. customyielding a precipitate, which
  10. filtrationis collected by filtration
  11. washwashed with water
  12. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-cf1e48bd96f048f38665f9ce555ebe5f
Source dataset
uspto-grants-2007_10
Patent number
US07282595B2

Reaction notes

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