Phosphorus oxychloride → 4-Chloro-3-phenylthieno[2,3-b]pyridine

HRID 2104103Notes

Reaction equation

HRID 2104103 reaction equation
[C:1]1([C:7]2[C:15]3[C:14](=O)[CH:13]=[CH:12][NH:11][C:10]=3[S:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:19])=O>>[Cl:19][C:14]1[CH:13]=[CH:12][N:11]=[C:10]2[S:9][CH:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:15]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 684349933-phenyl-7H-thieno[2,3-b]pyridine-4-one

Product 1

HCID 684343754-Chloro-3-phenylthieno[2,3-b]pyridine

Procedure

3-Phenyl-7H-thieno[2,3-b]pyridine-4-one (0.7 g, 4.29 mmol) was added to phosphorous oxychloride (10 ml) and heated to reflux for 4 hr. The solvent was removed to near dryness and the residue dissolved in DCM. The solution was washed with water followed by saturated sodium hydrogen carbonate and dried over magnesium sulfate. The solution was filtered through a pad of silica and solvents removed in vacuo to give 4-chloro-3-phenyl-thieno[2,3-b]pyridine. Yield=0.261g (25%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hr
  3. customThe solvent was removed
  4. dissolutionthe residue dissolved in DCM
  5. washThe solution was washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationThe solution was filtered through a pad of silica and solvents
  8. customremoved in vacuo

Sources & evidence

ORD record
ord-fdcd22a8533a47e981cc2806ca9c738b
Source dataset
uspto-grants-2009_08
Patent number
US07576212B2

Reaction notes

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