Hydrochloric Acid → HCID 19963320, compound

HRID 1720446Notes

Reaction equation

HRID 1720446 reaction equation
[I:1][C:2]1[S:3][C:4]([CH:7]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)O)=[CH:5][CH:6]=1.O.O.[Sn](Cl)Cl.Cl.[OH-].[Na+]>C(O)(=O)C.O>[I:1][C:2]1[S:3][C:4]([CH2:7][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 19963288HCID 19963288, compound

Product 1

HCID 19963320HCID 19963320, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A suspension of 2-iodo-5-(4-pyridylhydroxymethyl)thiophene (0.65 g, 2.05 mmol) and tin(II) chloride dihydrate (1.01 g, 4.51 mmol) in acetic acid (5 mL) was treated with HCl gas for 10 rain and stirred for 2 hours at ambient temperature. The reaction mixture was poured into H2O, neutralized with 10% aqueous NaOH, and extracted twice with ethyl acetate. The combined organic layers were washed with H2O, dried over MgSO4, filtered, and concentrated in vacuo. Chromatography on silica gel provided 2-iodo-5-(4-pyridylmethyl)thiophene (0.22 g, 36% yield) as a white solid.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic layers were washed with H2O
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d4797e1dea084bd5bf74e9ceac81449f
Source dataset
uspto-grants-1996_04
Patent number
US05506261

Reaction notes

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