HCID 13923710, compound → HCID 13923711, compound

HRID 2118451Notes

Reaction equation

HRID 2118451 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH:14]C(C)(C)C)(=[O:13])=[O:12]>FC(F)(F)C(O)=O>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH2:14])(=[O:13])=[O:12]

Participants

3

Reactant 1

HCID 13923710HCID 13923710, compound

Product 1

HCID 13923711HCID 13923711, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the crude ether from Example 2 (35.0 g) and 80 ml trifluoroacetic acid was stirred at room temperature for 16 hours. The trifluoroacetic acid was removed in vacuo and methylene chloride added to the residue. The organic phase was washed twice with cold saturated sodium bicarbonate, once with water and dried (Na2SO4). Concentration gave a viscous brown oil which was triturated with hexane. The resulting sticky solid was recrystallized from chloroform/hexane (1:1) to provide 11.0 g of pure 2-(2-methoxyethyl)benzenesulfonamide as a white solid; m.p. 79-81.

Workup

  1. customThe trifluoroacetic acid was removed in vacuo and methylene chloride
  2. additionadded to the residue
  3. washThe organic phase was washed twice with cold saturated sodium bicarbonate, once with water
  4. dry with materialdried (Na2SO4)
  5. concentrationConcentration
  6. customgave a viscous brown oil which
  7. customwas triturated with hexane
  8. customThe resulting sticky solid was recrystallized from chloroform/hexane (1:1)

Sources & evidence

ORD record
ord-35e8ce74838148389a7fd71f81cf5998
Source dataset
uspto-grants-1987_07
Patent number
US04678502

Reaction notes

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