Phosphorus oxychloride → HCID 19809387, compound
Reaction equation
[CH2:1]([C:3]1[NH:4][C:5](=O)[C:6]2[S:7][CH2:8][C:9](=[O:14])[N:10]([CH3:13])[C:11]=2[N:12]=1)[CH3:2].P(Cl)(Cl)([Cl:18])=O>>[Cl:18][C:5]1[C:6]2[S:7][CH2:8][C:9](=[O:14])[N:10]([CH3:13])[C:11]=2[N:12]=[C:3]([CH2:1][CH3:2])[N:4]=1Participants
Procedure
The 6,7-dihydro-2-ethyl-8-methyl-3H-pyrimido- ]5,4-b][1,4]thiazine-4,7-dione of Example 115 (2.7 g, 12.04 mmole) was suspended in approximately 150 ml of phosphorus oxychloride and refluxed for about 20 hours. The solution was concentrated in vacuo and the excess phosphorus oxychloride was decomposed with the careful addition of ice and water. The aqueous solution was neutralized with the cautious addition of concentrated ammonium hydroxide, followed by the addition of sodium bicarbonate. The aqueous solution was extracted numerous times with chloroform; the extracts were combined, washed well with water, then brine, dried over magnesium sulfate, filtered and evaporated in vacuo to provide 2.4 g (83%) of an off-white solid. The structural assignment was confirmed by infrared and nuclear magnetic resonance spectral analyses.
Workup
- temperaturerefluxed for about 20 hours
- concentrationThe solution was concentrated in vacuo
- additionthe excess phosphorus oxychloride was decomposed with the careful addition of ice and water
- additionThe aqueous solution was neutralized with the cautious addition of concentrated ammonium hydroxide
- additionfollowed by the addition of sodium bicarbonate
- extractionThe aqueous solution was extracted numerous times with chloroform
- washwashed well with water
- dry with materialbrine, dried over magnesium sulfate
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-8d22a5b209bd4f74a16d7495a4572574
- Source dataset
- uspto-grants-1992_11
- Patent number
- US05166343
Reaction notes
Loading…