Ammonia → HCID 63075568, compound

HRID 2247628Notes

Reaction equation

HRID 2247628 reaction equation
C1COCC1.[F:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([F:16])[C:14]=1[F:15])[CH:10]=O.C[Si]([C:21]#[N:22])(C)C.[NH3:23]>C(O)C.[I-].[Zn+2].[I-]>[NH2:23][CH:10]([C:9]1[CH:8]=[C:7]([F:6])[C:14]([F:15])=[C:13]([F:16])[CH:12]=1)[C:21]#[N:22]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 82115Trimethylsilyl cyanideHCID 27769543,4,5-Trifluorobenzaldehyde

Product 1

HCID 63075568HCID 63075568, compound

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 702EthanolSolvent

Procedure

To a THF solution (20 mL) of 3,4,5-trifluorobenzaldehyde (1.3 g), trimethylsilylcyanide (1.35 mL) and zinc iodide (259 mg) were added, and the reaction solution was agitated at room temperature for 40 minutes. 2N ammonia solution in ethanol (15 mL) was added to the reaction solution, and the reaction solution was agitated at 50° C. for 4 hours. The reaction mixture was allowed to cool to room temperature, and the solvent was removed under reduced pressure. Ethyl acetate and saturated sodium bicarbonate water were added to the residue, and the organic layer was partitioned. The organic layer obtained was dried over magnesium sulfate, the solvent was removed under reduced pressure, and 780 mg of the title compound was obtained by purifying the residue with silica gel chromatography (Carrier: Chromatorex, elution solvent: heptane-ethyl acetate system). The physical properties of the compound are as follows.

Workup

  1. stirringthe reaction solution was agitated at 50° C. for 4 hours
  2. temperatureto cool to room temperature
  3. customthe solvent was removed under reduced pressure
  4. additionEthyl acetate and saturated sodium bicarbonate water were added to the residue
  5. customthe organic layer was partitioned
  6. customThe organic layer obtained
  7. dry with materialwas dried over magnesium sulfate
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2ac436356aa04652b3c67b484b1bb6d3
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

Loading…