Oxalyl chloride → 2-Cyano-4-(trifluoromethyl)-5-pyrimidinecarbonyl chloride

HRID 2394274Notes

Reaction equation

HRID 2394274 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

Reactant 2

HCID 65578Oxalyl chlorideHCID 105848562-Cyano-4-(trifluoromethyl)-5-pyrimidinecarboxylic acid

Product 1

HCID 107997692-Cyano-4-(trifluoromethyl)-5-pyrimidinecarbonyl chlorideYield 83.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 24526ChlorineSolvent

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

  1. concentrationThe reaction was concentrated
  2. 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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