3-(2,5,5-Trimethyl-1,3-dioxan-2-yl)thiophene-2-sulfonamide → 3-Acetyl-2-thiophenesulfonamide

HRID 1735987Notes

Reaction equation

HRID 1735987 reaction equation
[CH3:1][C:2]1([C:10]2[CH:14]=[CH:13][S:12][C:11]=2[S:15]([NH2:18])(=[O:17])=[O:16])OCC(C)(C)C[O:3]1>C1COCC1.Cl>[C:2]([C:10]1[CH:14]=[CH:13][S:12][C:11]=1[S:15]([NH2:18])(=[O:16])=[O:17])(=[O:3])[CH3:1]

Participants

4

Reactant 1

HCID 229019383-(2,5,5-Trimethyl-1,3-dioxan-2-yl)thiophene-2-sulfonamide

Product 1

HCID 229019263-Acetyl-2-thiophenesulfonamideYield 79%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product from Step A (174.05 g, crude) was dissolved in a mixture of THF (1000 mL) and 1N HCl (1000 mL) and heated at reflux temperature for 1.5 hr. The THF was evaporated and the aqueous solution made basic by the addition of a saturated aqueous sodium bicarbonate solution. The mixture was cooled and the precipitate collected by filtration, washed with cold water and dried in vacuo to give the crude product (109.1 g,). Recrystallization from acetonitrile gave the desired product (81.5 g, 79%): mp 193°-196° C.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 1.5 hr
  3. customThe THF was evaporated
  4. additionby the addition of a saturated aqueous sodium bicarbonate solution
  5. temperatureThe mixture was cooled
  6. filtrationthe precipitate collected by filtration
  7. washwashed with cold water
  8. customdried in vacuo
  9. customto give the crude product (109.1 g,)
  10. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-a3f062ca59674ecb9fa508a3b1bad15d
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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