Phosphorus oxychloride → HCID 89929698, compound

HRID 2178986Notes

Reaction equation

HRID 2178986 reaction equation
[C:1]12[C:12](O)=[CH:11][CH:10]=[N:9][C:8]=1[S:7][C:6]1[CH2:5][CH2:4][CH2:3][C:2]2=1.P(Cl)(Cl)([Cl:16])=O>O1CCOCC1>[Cl:16][C:12]1[C:1]2[C:2]3[CH2:3][CH2:4][CH2:5][C:6]=3[S:7][C:8]=2[N:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178516473HCID 178516473, compound

Product 1

HCID 89929698HCID 89929698, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 7-thia-9-azatricyclo[6.4.0.0^[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-ol (280 mg, 1.46 mmol, 1.00 equiv) in 1,4-dioxane (10 mL) was added phosphoroyl trichloride (1.12 g, 7.30 mmol, 5.00 equiv) at room temperature under nitrogen. The resulting solution was stirred for 2 h at 90° C. in an oil bath and concentrated under reduced pressure. The pH value of the solution was adjusted to 8 with saturated aqueous sodium bicarbonate and extracted with 3×30 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10) to afford 12-chloro-7-thia-9-azatricyclo[6.4.0.0^[2,6]]dodeca-1(8),2(6),9,11-tetraene (0.25 g, 81%) as a white solid. MS (ES): m/z 210 and 212 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with 3×30 mL of ethyl acetate
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cc2de7d3c26347a2ba6a0cfa62a3fe76
Source dataset
uspto-grants-2015_06
Patent number
US09067948B2

Reaction notes

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