N,N-Diethylaniline → HCID 21716192, compound

HRID 1385943Notes

Reaction equation

HRID 1385943 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8]CC#C)[C:5]([C:12]2[C:13](=[O:23])[N:14]([CH3:22])[C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=2)=[C:4]([F:24])[CH:3]=1.[F-].[Cs+].C(N(CC)[C:30]1[CH:35]=CC=C[CH:31]=1)C>>[Cl:1][C:2]1[C:7]2[CH:31]=[C:30]([CH3:35])[O:8][C:6]=2[C:5]([C:12]2[C:13](=[O:23])[N:14]([CH3:22])[C:15]([C:18]([F:20])([F:19])[F:21])=[CH:16][CH:17]=2)=[C:4]([F:24])[CH:3]=1

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 25953Cesium fluorideHCID 18408355HCID 18408355, compound

Product 1

HCID 21716192HCID 21716192, compoundYield 21%

Procedure

2.78 g (7.73 mmol) of 3-[4-chloro-2-fluoro-6-propargyloxyphenyl]-1-methyl-6-trifluoromethyl-2(1H)-pyridone and 2.35 g (15.46 mmol) of cesium fluoride was heated to 180° C. in 50 ml of N,N-diethylaniline and reacted for 1 hour. The solvent was distilled off under reduced pressure, followed by extraction with ethyl acetate. The organic layer was washed with dilute hydrochloric acid and dried over magnesium sulfate. Then, the solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.58 g (yield: 21%) of the desired product. Melting point: 138-140° C.

Workup

  1. customreacted for 1 hour
  2. distillationThe solvent was distilled off under reduced pressure
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with dilute hydrochloric acid
  5. dry with materialdried over magnesium sulfate
  6. distillationThen, the solvent was distilled off under reduced pressure
  7. customThen, the obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3cca48401d374bb1a7fa91097529225d
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

Loading…