Hydrogen iodide → HCID 20152693, compound

HRID 2283365Notes

Reaction equation

HRID 2283365 reaction equation
I.[N+:2]([C:5]1[CH:9]=[CH:8][S:7][C:6]=1[S:10]([NH2:13])(=[O:12])=[O:11])([O-])=O>C(OCC)(=O)C>[NH2:2][C:5]1[CH:9]=[CH:8][S:7][C:6]=1[S:10]([NH2:13])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 24841Hydrogen iodideHCID 57750963HCID 57750963, compound

Product 1

HCID 20152693HCID 20152693, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A 57% aqueous solution of hydriodic acid (15 mL) was added to neat 3-nitro-thiophene-2-sulfonamide (1.02 g, 4.90 mmol) at room temperature. The reaction mixture was heated at 90° C. for 1 hour, cooled to room temperature and diluted with ethyl acetate (50 mL). The mixture was washed with a solution of sodium thiosulfate and the pH was adjusted to pH˜8 with sodium bicarbonate. The mixture was extracted with 10% methanol in ethyl acetate and the organic phase was dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography, using a gradient of 30-70% ethyl acetate in hexanes as the eluent, gave 65% yield of the title compound.

Workup

  1. temperaturecooled to room temperature
  2. washThe mixture was washed with a solution of sodium thiosulfate
  3. extractionThe mixture was extracted with 10% methanol in ethyl acetate
  4. dry with materialthe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-944183c50aec48a7b5122936c9ab87e5
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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