Hydrochloric Acid → HCID 49757460, compound

HRID 227644Notes

Reaction equation

HRID 227644 reaction equation
[H-].[Na+].[C:3]([CH2:5][C:6]([O:8][CH3:9])=[O:7])#[N:4].[H][H].Cl[C:13]1[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][N:14]=1.Cl>CN(C=O)C.O.CO>[CH3:9][O:8][C:6](=[O:7])[CH:5]([C:13]1[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:21])[F:22])=[CH:15][N:14]=1)[C:3]#[N:4]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7747Methyl cyanoacetateHCID 24758Sodium hydrideHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 49757460HCID 49757460, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Under argon, 116 g of sodium hydride 60% in dispersion in oil (2.91 mol, 1.8 eq.) was suspended in 3 L of DMF. The suspension was cooled down in an ice-water bath. 160 g (1.616 mol, 1.0 eq) of methyl cyanoacetate in solution in 200 mL of DMF was added dropwise under stirring. Temperature rose to 50° C. and hydrogen was released. Once bubbling was over, 350 g (1.616 mol, 1.0 eq) of 2,3-dichloro-5-(trifluoromethyl)-pyridine was added under stirring. The mixture was stirred overnight at room temperature. 50 mL of methanol were added dropwise to quench the reaction. The reaction mixture was poured in 5 L of water. pH was adjusted to 3-4 with concentrated hydrochloric acid.

Workup

  1. temperatureThe suspension was cooled down in an ice-water bath
  2. customrose to 50° C.
  3. customOnce bubbling
  4. additionwas added
  5. stirringunder stirring
  6. stirringThe mixture was stirred overnight at room temperature
  7. customto quench
  8. customthe reaction

Sources & evidence

ORD record
ord-9225dd8c572d4d24a0e294d3dfb8db85
Source dataset
uspto-grants-2009_07
Patent number
US07560567B2

Reaction notes

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