Ethanol → HCID 57562941, compound

HRID 1770819Notes

Reaction equation

HRID 1770819 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([N+:13]([O-])=O)[CH:8]=[C:9]([CH3:12])[C:10]=1[F:11])(=[O:4])=[O:3].C(O)C.[Cl-].[NH4+]>[Fe].O>[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([CH:8]=[C:9]([CH3:12])[C:10]=1[F:11])[NH2:13])(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 57562895HCID 57562895, compound

Product 1

HCID 57562941HCID 57562941, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a heterogeneous solution of 3-aminosulfonyl-4-fluoro-5-methylnitrobenzene (27) (0.5 g, 2 mmol) in of ethanol:water (50 mL, each) were added iron powder (1.08 g, 20 mmol), and ammonium chloride (1.08 g, 20 mmol) at room temperature. The resulting heterogeneous mixture was then stirred at 60° C. for 2 hours, filtered through celite (when hot), washed with ethanol (2×50 mL) and then the solvent was removed under reduced pressure. The residue upon dilution with water was extracted with ethyl acetate (3×50 mL), and the organic phase was dried over anhydrous sodium sulfate and concentrated under a reduced pressure to obtain 3-aminosulfonyl-4-fluoro-5-methylaniline (28). LCMS: purity: 85%; MS (m/z): 205 (MH+).

Workup

  1. filtrationfiltered through celite (when hot)
  2. washwashed with ethanol (2×50 mL)
  3. customthe solvent was removed under reduced pressure
  4. extractionThe residue upon dilution with water was extracted with ethyl acetate (3×50 mL)
  5. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-5636bb7326d3455a9c43ca8a48dd1cd9
Source dataset
uspto-grants-2016_02
Patent number
US09248190B2

Reaction notes

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