Sulfuric Acid → HCID 14700393, compound

HRID 1651650Notes

Reaction equation

HRID 1651650 reaction equation
S(=O)(=O)(O)O.O[CH:7]([C:9]1[CH:10]=[C:11]([S:18]([NH2:21])(=[O:20])=[O:19])[S:12][C:13]=1[S:14]([CH3:17])(=[O:16])=[O:15])[CH3:8].C([O-])(O)=[O:23].[Na+].[C:27](#[N:29])[CH3:28]>>[C:27]([NH:29][CH:7]([C:9]1[CH:10]=[C:11]([S:18]([NH2:21])(=[O:20])=[O:19])[S:12][C:13]=1[S:14]([CH3:17])(=[O:16])=[O:15])[CH3:8])(=[O:23])[CH3:28]

Participants

5

Reactant 4

HCID 1118Sulfuric Acid2×HCID 6342Acetonitrile2×HCID 516892Sodium BicarbonateHCID 14700390HCID 14700390, compound

Product 1

HCID 14700393HCID 14700393, compoundYield 34%

Procedure

To acetonitrile (30 ml) was added concentrated sulfuric acid (2.94 g, 0.03 mol) followed by 4-(1-hydroxyethyl)-5-methylsulfonylthiophene-2-sulfonamide (2.85 g, 0.01 mol). The resulting solution was stirred at room temperature for 24 hours. Only about 1/2 of the alcohol had reacted so additional sulfuric acid (2.94 g, 0.03 mol) was added. After another 16 hours at room temperature the reaction was complete. The mixture was basified with excess NaHCO3. Acetonitrile (100 ml) was added, the mixture was filtered and the acetonitrile was evaporated in vacuo. The residue was taken up in ethyl acetate, washed with saturated NaCl solution, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The solid obtained was recrystallized from water to give 1.1 g (34%) of yellow solid, m.p. 114-117° C. HPLC and TLC confirmed the purity and NMR confirmed the structure.

Workup

  1. additionwas added
  2. waitAfter another 16 hours at room temperature the reaction was complete
  3. filtrationthe mixture was filtered
  4. customthe acetonitrile was evaporated in vacuo
  5. washwashed with saturated NaCl solution
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe solid obtained
  10. customwas recrystallized from water

Sources & evidence

ORD record
ord-59a9af6bc808489f93eff32964720c5b
Source dataset
uspto-grants-1990_05
Patent number
US04929637

Reaction notes

Loading…