Phosphorus oxychloride → 7-Chloro-6-nitrothieno[3,2-b]pyridine

HRID 711928Notes

Reaction equation

HRID 711928 reaction equation
[N+:1]([C:4]1[C:5](O)=[C:6]2[S:12][CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2].P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=[C:7]2[CH:10]=[CH:11][S:12][C:6]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526786HCID 178526786, compound

Product 1

HCID 142079507-Chloro-6-nitrothieno[3,2-b]pyridineYield 75%

Procedure

6-Nitrothieno[3,2-b]pyridin-7-ol (3.3 g, 17 mmol) was suspended in phosphoryl chloride (30 mL, 400 mmol) and heated at reflux for 1 h (dissolution was apparent after 45 min) The solvent was removed. Toluene was added to the residue and the volatiles were removed in vacuo. Dichloromethane and sat. NaHCO3 solution were added (Caution: gas evolution), and the layers separated. The organic layer was washed with water, dried over MgSO4 and concentrated to give the desired product (2.7 g, 75%). LCMS calculated for C7H4ClN2O2S (M+H)+: m/z=215.0. Found: 214.9.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 h
  3. dissolution(dissolution was apparent after 45 min) The solvent
  4. customwas removed
  5. additionToluene was added to the residue
  6. customthe volatiles were removed in vacuo
  7. additionDichloromethane and sat. NaHCO3 solution were added (Caution: gas evolution)
  8. customthe layers separated
  9. washThe organic layer was washed with water
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-1680e72ec26941ce831b41b1c96a5192
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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