Pyruvic Acid → N-[4-CYANO-3-(TRIFLUOROMETHYL)PHENYL]-2-OXOPROPANAMIDE

HRID 1018157Notes

Reaction equation

HRID 1018157 reaction equation
[C:1]([OH:6])(=O)[C:2]([CH3:4])=[O:3].S(Cl)(Cl)=O.[C:11]([C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][C:14]=1[C:20]([F:23])([F:22])[F:21])#[N:12]>CC(N(C)C)=O.CCOCC>[C:11]([C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:1](=[O:6])[C:2](=[O:3])[CH3:4])=[CH:15][C:14]=1[C:20]([F:21])([F:22])[F:23])#[N:12]

Participants

6

Reactant 3

HCID 1060Pyruvic AcidHCID 24386Thionyl ChlorideHCID 5221704-Amino-2-(trifluoromethyl)benzonitrile

Product 1

HCID 9899821N-[4-CYANO-3-(TRIFLUOROMETHYL)PHENYL]-2-OXOPROPANAMIDE

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 31374DimethylacetamideSolvent

Procedure

Pyruvic acid (3.0 mL; 43 mmol) and thionyl chloride (3.1 mL; 43 mmol) were added simultaneously via syringes to a stirring solution of 4-cyano-3-trifluoromethyl-aniline (1.00 g; 5.38 mmol) in 20 mL of dry DMA at room temperature. After 10 minutes, the reaction mixture was diluted with ether and extracted 3 times with saturated NaHCO3 and 4 times with cold saturated brine. The organic layer was dried with MgSO4 and concentrated by rotary evaporation. The product was purified by silica gel chromatography (ethyl acetate/hexanes [1/1]). Yield 1.11 g (81%); mp 147-148° C.; MS (FAB+) 257 (M+1); 1H NMR δ 9.12 (s, 1H), 8.15 (s, 1H), 8.01 (d, J=8.5), 7.84 (d, J=8.5, 1H), 2.59 (s, 3H); 13C NMR δ 195.66, 157.71, 140.29, 135.90, 134.2, 122.01, 121.85, 117.44, 115.12, 105.55, 23.92; 19F NMR δ −62.76. IR: 3330, 3112, 3065, 1719, 1540. UV: λmax 214, 248, 288. Anal. Calculated for C11H7F3N2O2: C, 51.57; H, 2.75; N, 10.94. Found: C, 51.69; H, 2.81; N, 10.86.

Workup

  1. extractionextracted 3 times with saturated NaHCO3 and 4 times with cold saturated brine
  2. dry with materialThe organic layer was dried with MgSO4
  3. concentrationconcentrated by rotary evaporation
  4. customThe product was purified by silica gel chromatography (ethyl acetate/hexanes [1/1])

Sources & evidence

ORD record
ord-1bb0416b32544c9f914a4bb72aa4d9e7
Source dataset
uspto-grants-2002_11
Patent number
US06479692B1

Reaction notes

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