Hydrochloric Acid → HCID 14700404, compound

HRID 1651658Notes

Reaction equation

HRID 1651658 reaction equation
[C:1]([NH:4][CH:5]([C:7]1[CH:8]=[C:9]([S:17]([NH2:20])(=[O:19])=[O:18])[S:10][C:11]=1[S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])[CH3:6])(=O)[CH3:2].Cl>O1CCCC1.C(OCC)(=O)C>[CH2:1]([NH:4][CH:5]([C:7]1[CH:8]=[C:9]([S:17]([NH2:20])(=[O:19])=[O:18])[S:10][C:11]=1[S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])[CH3:6])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 14700403HCID 14700403, compound

Product 1

HCID 14700404HCID 14700404, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred, refluxing suspension of 4-(1-acetamidoethyl)-5-ethylsulfonylthiophene-2-sulfonamide (2.61 g, 0.0077 mol) in dry tetrahydrofuran under nitrogen atmosphere was added dropwise over 1/2 hour a solution of dimethylsulfide borane complex (2.3 ml of a 10 M solution, 0.023 mol) in dry THF (10 ml). The cloudy solution which formed was stirred at reflux for 11/2 hours. The mixture was cooled in ice and acidified by the dropwise addition of 6N HCl (10 ml), and concentrated in vacuo at room temperature. The moist solid residue was basified with saturated NaHCO3 and was extracted with ethyl acetate (4×50 ml). The amino product was extracted into 3N HCl (4×25 ml). The combined HCl extracts were neutralized with NaHCO3 and extracted with ethyl acetate (4×50 ml). The ethyl acetate extract was dried over anhydrous Na2SO4, filtered and concentrated in vacuo at room temperature. A colorless oil was obtained which solidified to a white solid upon trituration in ethyl acetate. The crude yield was 1.99 g or 80%. The solid after recrystallization from ethyl acetate had m.p. 135-137.5° C. NMR supported the structure and HPLC confirmed the purity.

Workup

  1. temperatureTo a stirred, refluxing
  2. customThe cloudy solution which formed
  3. temperatureat reflux for 11/2 hours
  4. temperatureThe mixture was cooled in ice
  5. concentrationconcentrated in vacuo at room temperature
  6. extractionwas extracted with ethyl acetate (4×50 ml)
  7. extractionThe amino product was extracted into 3N HCl (4×25 ml)
  8. extractionextracted with ethyl acetate (4×50 ml)
  9. extractionThe ethyl acetate extract
  10. dry with materialwas dried over anhydrous Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo at room temperature
  13. customA colorless oil was obtained which
  14. customThe solid after recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-f9333450e56a445bbf2f7b2860e1d54f
Source dataset
uspto-grants-1990_05
Patent number
US04929637

Reaction notes

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