Phosphorus oxychloride → HCID 57756255, compound

HRID 227764Notes

Reaction equation

HRID 227764 reaction equation
[C:1]1([C:7]2[C:8]3[CH:16]=[CH:15][S:14][C:9]=3[C:10](=O)[NH:11][N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=P(Cl)(Cl)[Cl:19]>>[Cl:19][C:10]1[C:9]2[S:14][CH:15]=[CH:16][C:8]=2[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:12][N:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12796535HCID 12796535, compound

Product 1

HCID 57756255HCID 57756255, compound

Procedure

To 4-phenylthieno[2,3-d]pyridazin-7(6H)-one (0.714 g, 3.13 mmol) was added POCl3 (2.92 ml, 31.3 mmol). A water condenser was attached to the reaction flask and the mixture was heated to reflux for 15.5 hours. The reaction was concentrated and diluted with CH2Cl2 and ice water. The mixture was basified with solid sodium bicarbonate. The organic layers were separated and dried over sodium sulfate. To the residual crude after concentration, 50% EtOAc was added and the solution was filtered through a pad of silica gel. The product fraction were concentrated to yield 7-chloro-4-phenylthieno[3,2-d]pyridazine as a light yellow solid. MS m/z=247 [M+1]+. Calc'd for C12H7N2S: 246.71.

Workup

  1. customA water condenser was attached to the reaction flask
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 15.5 hours
  4. concentrationThe reaction was concentrated
  5. additiondiluted with CH2Cl2 and ice water
  6. customThe organic layers were separated
  7. dry with materialdried over sodium sulfate
  8. concentrationTo the residual crude after concentration, 50% EtOAc
  9. additionwas added
  10. filtrationthe solution was filtered through a pad of silica gel
  11. concentrationThe product fraction were concentrated

Sources & evidence

ORD record
ord-96d4ae50c8574ea68c99809784875a94
Source dataset
uspto-grants-2009_07
Patent number
US07560551B2

Reaction notes

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