Sodium Carbonate → 2-Amino-4-chloro-6-cyano-[1,3,5]triazine
Reaction equation
[NH2:1][C:2]1[NH:3][C:4](=O)[N:5]=[C:6]([C:8]#[N:9])[N:7]=1.P(Cl)(Cl)([Cl:13])=O.C(=O)([O-])[O-].[Na+].[Na+]>>[NH2:1][C:2]1[N:3]=[C:4]([Cl:13])[N:5]=[C:6]([C:8]#[N:9])[N:7]=1Participants
4
Procedure
To 2-amino-4-cyano-6-oxo-1,3,5-triazine (J. Am. Chem. Soc., 1961, 83, 1261-2, 2.30 g, 16.8 mmol) was added phosphoryl trichloride (50 mL, 547 mmol) and the mixture heated at 90 C for 2 h. The reaction mixture was cooled to room temperature before pouring onto ice-water (250 mL) and basifying to pH 8 with solid sodium carbonate. The mixture was then extracted into DCM (3×250 mL) and the combined organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the desired compound, which was used crude without further purification (343 mg, 13%). Method C HPLC-MS: 2 MH+ requires m/z=311. Found: m/z=311, Rt=0.74 min (100%).
Workup
- temperaturethe mixture heated at 90 C for 2 h
- additionbefore pouring onto ice-water (250 mL)
- extractionThe mixture was then extracted into DCM (3×250 mL)
- dry with materialthe combined organics were dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-db512cb438324479b5a864c1065ab6f9
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895733B2
Reaction notes
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