Pyridine → 5-(3-Acetyloxypropanesulfonyl)thiophene-2-sulfonamide

HRID 2414133Notes

Reaction equation

HRID 2414133 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][S:5]([C:8]1[S:12][C:11]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6].N1C=CC=CC=1.[C:23](Cl)(=[O:25])[CH3:24]>C1COCC1>[C:23]([O:1][CH2:2][CH2:3][CH2:4][S:5]([C:8]1[S:12][C:11]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6])(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 155993805-(3-Hydroxypropanesulfonyl)thiophene-2-sulfonamide

Product 1

HCID 155993855-(3-Acetyloxypropanesulfonyl)thiophene-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(3-hydroxypropanesulfonyl)thiophene-2-sulfonamide (1.2 g, 4.2 mmol) in 75 ml of THF was added 0.5 ml of pyridine and 0.5 ml of acetyl chloride. The reaction mixture was stirred for 18 hours at room temperature. The reaction mixture was filtered and the filtrate was concentrated under vacuum. The oily residue was dissolved in ethyl acetate and the ethyl acetate was washed with aqueous sodium bicarbonate solution and then brine. After drying over sodium sulfate the ethyl acetate was concentrated under vacuum, giving a solid residue. This solid was recrystallized from dichloroethane to give 1.0 g of product; m.p. 103°-104.5°. 1H-NMR,δ (DMSO, d6) 7.97 (2H, S); 7.75 (1H, d, J=3); 7.57 (lH, d, J=3); 4.00 (2H, t, J=6); 3.50 (2H, m); 1.90 (5H, m).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under vacuum
  3. dissolutionThe oily residue was dissolved in ethyl acetate
  4. washthe ethyl acetate was washed with aqueous sodium bicarbonate solution
  5. dry with materialAfter drying over sodium sulfate the ethyl acetate
  6. concentrationwas concentrated under vacuum
  7. customgiving a solid residue
  8. customThis solid was recrystallized from dichloroethane

Sources & evidence

ORD record
ord-88b4bba0da8b47d9a415dcd7ca286aeb
Source dataset
uspto-grants-1988_01
Patent number
US04721794

Reaction notes

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