Sulfuric Acid → HCID 14700403, compound

HRID 1651657Notes

Reaction equation

HRID 1651657 reaction equation
[C:1](#[N:3])[CH3:2].S(=O)(=O)(O)[OH:5].[CH2:9]([S:11]([C:14]1[S:18][C:17]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:16][C:15]=1[CH:23](O)[CH3:24])(=[O:13])=[O:12])[CH3:10].C([O-])(O)=O.[Na+]>O>[C:1]([NH:3][CH:23]([C:15]1[CH:16]=[C:17]([S:19]([NH2:22])(=[O:20])=[O:21])[S:18][C:14]=1[S:11]([CH2:9][CH3:10])(=[O:12])=[O:13])[CH3:24])(=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 23050260HCID 23050260, compound

Product 1

HCID 14700403HCID 14700403, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To acetonitrile (40 ml) was added concentrated sulfuric acid (8.1 g, 0.0828 mol). Then 5-ethylsulfonyl-4-(1-hydroxyethyl)thiophene-2-sulfonamide (4.14 g, 0.0138 mol) was added and the solution was stirred at room temperature until no starting material remained (48 hours). The solution was neutralized by adding solid NaHCO3 along with water (5 ml). The mixture was filtered and the solids were washed with acetonitrile. The filtrate and washings were concentrated in vacuo to an oil. This residual oil was taken up in ethyl acetate (125 ml). The extract was washed with saturated NaCl, dried over anhydrous Na2SO4, filtered and concentrated in vacuo at room temperature, to give 2.74 g (58%) of white solid which was a single product by TLC, m.p. 213-220° C. NMR supported the structure.

Workup

  1. custom(48 hours)
  2. filtrationThe mixture was filtered
  3. washthe solids were washed with acetonitrile
  4. concentrationThe filtrate and washings were concentrated in vacuo to an oil
  5. washThe extract was washed with saturated NaCl
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo at room temperature

Sources & evidence

ORD record
ord-b5de5d5f0a0d4986b871f90fb194681e
Source dataset
uspto-grants-1990_05
Patent number
US04929637

Reaction notes

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