Oxalyl chloride → 2-Cyano-4-(trifluoromethyl)-5-pyrimidinecarbonyl chloride
Reaction equation
[C:1]([C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([C:13]([OH:15])=O)=[CH:5][N:4]=1)#[N:2].C(Cl)(=O)C([Cl:19])=O>CN(C=O)C.ClCl>[C:1]([C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([C:13]([Cl:19])=[O:15])=[CH:5][N:4]=1)#[N:2]Participants
5
Procedure
A solution of 2-cyano-4-trifluoromethylpyrimidine-5-carboxylic acid (2.0 g, 9.2 mmol), oxalyl chloride (1.4 g, 11 mmol) and DMF (4 drops) in CH2 Cl2 (46 mL) was stirred at room temperature under N2 for 0.75 h. The reaction was concentrated and distilled (b.p. 100° C., 1.5 mm/Hg) to give the title compound (1.8 g, 82% yield); 1HNMR (CDCl3) δ 9.49 (s, 1H).
Workup
- concentrationThe reaction was concentrated
- distillationdistilled (b.p. 100° C., 1.5 mm/Hg)
Sources & evidence
- ORD record
- ord-dd830d0144254084ac1e1e3106c68e28
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05811428
Reaction notes
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