Phosphorus oxychloride → Imidazo[1,2-a]pyridine-3-sulfonyl chloride

HRID 2374138Notes

Reaction equation

HRID 2374138 reaction equation
[N:1]1[CH:2]=[C:3]([S:10]([OH:13])(=O)=[O:11])[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.P(Cl)(Cl)([Cl:16])=O>C(Cl)Cl>[N:1]1[CH:2]=[C:3]([S:10]([Cl:16])(=[O:13])=[O:11])[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 14422414Imidazo[1,2-a]pyridine-3-sulfonic acid

Product 1

HCID 53256697Imidazo[1,2-a]pyridine-3-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Step 1 (0.10 g, 0.5 mmol) was treated with phosphorus oxychloride (3 mL) and heated to reflux overnight. The reaction mixture was cooled to RT and treated with DCM (50 mL), poured into ice-water (100 mL), and then extracted with DCM (4×100 mL). The organic layers were combined and dried (Na2SO4), filtered, and concentrated to dryness under vacuum to give the title compound (0.10 g). 1H NMR (DMSO-d6) δ 8.87 (m, 1 H), 8.25 (s, 1 H), 7.98 (m, 2 H), 7.57 (m, 1 H).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. extractionextracted with DCM (4×100 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-dc13e6a01b62463c8b0b6061a98d77ae
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Reaction notes

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