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

HRID 2414134Notes

Reaction equation

HRID 2414134 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.[CH3:23][O:24][CH2:25][C:26](Cl)=[O:27]>C1COCC1.ClC(Cl)C>[CH3:23][O:24][CH2:25][C:26]([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:27]

Participants

6

Reactant 3

HCID 1049PyridineHCID 96623Methoxyacetyl chlorideHCID 155993805-(3-Hydroxypropanesulfonyl)thiophene-2-sulfonamide

Product 1

HCID 155993865-(3-Methoxyacetyloxypropanesulfonyl)thiophene-2-sulfonamide

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(3-hydroxypropane sulfonyl)thiophene-2-sulfonamide (1.2 g, 4.2 mmol) in 75 ml of THF was added 0.4 ml of pyridine and 0.5 g of methoxyacetyl 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 water and then brine. After drying over sodium sulfate the ethyl acetate was concentrated under vacuum, giving an oily residue. A crystalline product was obtained by dissolving the oil in hot dichloroethane and then cooling to 0° C. The yield was 0.8 g. m.p. 93°-95° C. 1H-NMR, δ (DMSO, d6) 8.00 (2H, s); 7.80 (1H, d, J=3); 7.63 (1H, d, J=3); 4.12 (2H, t, J=6); 4.00 (2H, s); 3.55 (2H, m); 3.27 (3H, s); 1.91 (2H, 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 water
  5. dry with materialAfter drying over sodium sulfate the ethyl acetate
  6. concentrationwas concentrated under vacuum
  7. customgiving an oily residue
  8. customA crystalline product was obtained
  9. temperaturecooling to 0° C

Sources & evidence

ORD record
ord-f0ee79ba02b64b11aa5175b6e341dadf
Source dataset
uspto-grants-1988_01
Patent number
US04721794

Reaction notes

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