Phosphorus oxychloride → 6-Chloro-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione
Reaction equation
[CH3:1][N:2]1[C:9](=O)[CH2:8][C:6](=[O:7])[N:5]([CH3:11])[C:3]1=[O:4].P(Cl)(Cl)([Cl:14])=O>O>[Cl:14][C:9]1[N:2]([CH3:1])[C:3](=[O:4])[N:5]([CH3:11])[C:6](=[O:7])[CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 1,3-dimethylbarbituric acid (20.0 g, 128.09 mmol) in water (10 ml), phosphorous oxychloride (80 ml) was added slowly by externally cooling and reaction was then refluxed for 3 h. The reaction mixture was allowed to cool to 0° C. and quenched with ice cold water (350 ml). The reaction mixture was extracted with chloroform (2×200 ml) and the combined organic extracts were washed with water, dried over Na2SO4 and concentrated to obtain 21.0 g of the product as a pale brown solid; 1H NMR (300 MHz, CDCl3) δ 3.33 (s, 3H), 3.57 (s, 3H), 5.94 (s, 1H).
Workup
- temperatureby externally cooling
- customreaction
- temperaturewas then refluxed for 3 h
- customquenched with ice cold water (350 ml)
- extractionThe reaction mixture was extracted with chloroform (2×200 ml)
- washthe combined organic extracts were washed with water
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d57353c61f1c42be8323e1f831281b35
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575178B2
Reaction notes
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