Sulfuric Acid → HCID 20033687, compound

HRID 231689Notes

Reaction equation

HRID 231689 reaction equation
OS(O)(=O)=O.O[CH:7]([C:9]1[CH:10]=[C:11]([S:25]([NH2:28])(=[O:27])=[O:26])[S:12][C:13]=1[S:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH3:8].C([O-])(O)=[O:30].[Na+].[C:34](#[N:36])[CH3:35]>O>[C:34]([NH:36][CH:7]([C:9]1[CH:10]=[C:11]([S:25]([NH2:28])(=[O:26])=[O:27])[S:12][C:13]=1[S:14]([C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1)(=[O:16])=[O:15])[CH3:8])(=[O:30])[CH3:35]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6342Acetonitrile2×HCID 516892Sodium BicarbonateHCID 20033668HCID 20033668, compound

Product 1

HCID 20033687HCID 20033687, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acetonitrile (30 ml) was cooled in ice and concentrated H2SO4 (4.4 ml, 0.083 mol) was added over about 5 minutes. Then 4-(1-hydroxyethyl)-5-(4-methoxyphenylsulfonyl)thiophene-2-sulfonamide (3.13 g, 0.0083 mol) in acetonitrile (20 ml) was added and the solution was stirred at room temperature over the week-end. The reaction was diluted with water (10 ml) and was neutralized with NaHCO3. The suspension was filtered and the solids were washed with acetonitrile. The filtrate and washings were concentrated in vacuo. The residual oil was taken up in ethyl acetate and water. The ethyl acetate was separated, washed with saturated NaCl, dried, filtered and concentrated in vacuo. A white solid foam was obtained, 3.18 g, yield 92%. The structure was supported by NMR analyses.

Workup

  1. filtrationThe suspension was filtered
  2. washthe solids were washed with acetonitrile
  3. concentrationThe filtrate and washings were concentrated in vacuo
  4. customThe ethyl acetate was separated
  5. washwashed with saturated NaCl
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customA white solid foam was obtained

Sources & evidence

ORD record
ord-5224ae8514ab418bb6c4023fc1649e9b
Source dataset
uspto-grants-1989_07
Patent number
US04847289

Reaction notes

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