Sulfuric Acid → HCID 23050272, compound

HRID 1651647Notes

Reaction equation

HRID 1651647 reaction equation
COCCOC[O:7][CH:8]([C:10]1[CH:11]=[C:12]([S:19]([NH2:22])(=[O:21])=[O:20])[S:13][C:14]=1[S:15]([CH3:18])(=O)=[O:16])[CH3:9].S(=O)(=O)(O)O.C([O-])(O)=O.[Na+]>CO>[OH:7][CH:8]([C:10]1[CH:11]=[C:12]([S:19]([NH2:22])(=[O:21])=[O:20])[S:13][C:14]=1[S:15]([CH3:18])=[O:16])[CH3:9]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 53862000HCID 53862000, compound

Product 1

HCID 23050272HCID 23050272, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-[1-(methoxyethoxymethoxy)ethyl]-5-methylsulfonylthiophene-sulfonamide (6.58 g, 0.0186 mol) in methanol (25 ml) was added dropwise over a 10 minute period a cold solution of 50% (by volume) sulfuric acid. The solution was stirred for an additional 20 minutes at room temperature. The reaction solution was basified with NaHCO3 with cooling and was concentrated to dryness in vacuo at 40° C. bath temperature. The solid residue was extracted with hot ethyl acetate and with 20% methanol/ethyl acetate. Concentration of the extracts in vacuo gave 4.0 g of solid which was purified by chromatography on silica gel using 5% methanol in methylene chloride. There was obtained 3.0 g (60%) of product, m.p. 172-185° C.

Workup

  1. temperaturewith cooling
  2. concentrationwas concentrated to dryness in vacuo at 40° C. bath temperature
  3. extractionThe solid residue was extracted with hot ethyl acetate and with 20% methanol/ethyl acetate

Sources & evidence

ORD record
ord-f8e9d2343e73421480f24a0933802832
Source dataset
uspto-grants-1990_05
Patent number
US04929637

Reaction notes

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