Hydrochloric Acid → HCID 14700394, compound

HRID 1651651Notes

Reaction equation

HRID 1651651 reaction equation
[C:1]([NH:4][CH:5]([C:7]1[CH:8]=[C:9]([S:16]([NH2:19])(=[O:18])=[O:17])[S:10][C:11]=1[S:12]([CH3:15])(=[O:14])=[O:13])[CH3:6])(=O)[CH3:2].Cl>O1CCCC1>[CH2:1]([NH:4][CH:5]([C:7]1[CH:8]=[C:9]([S:16]([NH2:19])(=[O:18])=[O:17])[S:10][C:11]=1[S:12]([CH3:15])(=[O:14])=[O:13])[CH3:6])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14700393HCID 14700393, compound

Product 1

HCID 14700394HCID 14700394, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred refluxing solution of 4-(1-acetamidoethyl)-5-methylsulfonylthiophene-2-sulfonamide (2.52 g, 0.0077 mol) in dry tetrahydrofuran (25 ml) under nitrogen atmosphere was added dropwise a solution of borane dimethylsulfide complex (2.3 ml, 0.023 mol) in THF (10 ml) over 1/2 hour. Reflux was continued for 1 hour. The solution was cooled in ice and acidified with 6N HCl (10 ml). The acidified solution was concentrated in vacuo. The residue was basified with saturated NaHCO3 solution and was extracted with ethyl acetate. The product was extracted into 3N HCl. This was again basified with saturated NaHCO3 solution, extracted with ethyl acetate, washed with saturated NaCl solution, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. A white solid was obtained (1.33 g) (55%), m.p. 162.5-165° C. Recrystallization from ethyl acetate gave 1.23 g of product, m.p. 164-165.5° C. HPLC and TLC confirmed the purity and NMR confirmed the structure.

Workup

  1. temperatureReflux
  2. temperatureThe solution was cooled in ice
  3. concentrationThe acidified solution was concentrated in vacuo
  4. extractionwas extracted with ethyl acetate
  5. extractionThe product was extracted into 3N HCl
  6. extractionextracted with ethyl acetate
  7. washwashed with saturated NaCl solution
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customA white solid was obtained (1.33 g) (55%), m.p. 162.5-165° C
  12. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-81dd3e037b6b4a0aa76e103989d0ce77
Source dataset
uspto-grants-1990_05
Patent number
US04929637

Reaction notes

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