Phosphorus oxychloride → HCID 21960234, compound

HRID 1633498Notes

Reaction equation

HRID 1633498 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[S:14][C:13]3[C:12](=O)[NH:11][CH:10]=[N:9][C:8]=3[CH:7]=2)=[CH:2]1.C(=O)(O)[O-].[Na+].P(Cl)(Cl)([Cl:23])=O>>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[S:14][C:13]3[C:12]([Cl:23])=[N:11][CH:10]=[N:9][C:8]=3[CH:7]=2)=[CH:2]1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 136184378HCID 136184378, compound

Product 1

HCID 21960234HCID 21960234, compoundYield 81%

Procedure

A solution of 6-(3-thienyl)-3H-thieno[3,2-d]pyrimid-4-one (218, 74 mg, 0.32 mmol) in phosphorus oxychloride (2 mL) under N2 was heated at reflux for 1 hour. The resulting solution was allowed to cool to room temperature, poured into a saturated aqueous solution of sodium bicarbonate to neutralize and then extracted with ethyl acetate. The organic layer was washed with water followed by saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and the solvent evaporated under reduced pressure to yield 6-(3-thienyl)-4-chlorothieno[3,2-d]pyrimidine (65 mg, 81% yield) as a yellow solid.

Workup

  1. temperatureat reflux for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-46cb85fb5cd14af292e54c38f7b08b90
Source dataset
uspto-grants-2003_01
Patent number
US06503914B1

Reaction notes

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