Phosphorus trichloride → N-(4-chloro-2-fluoro-5-propargyloxyphenyl)-2-(methoxyimino)acetamide

HRID 1510926Notes

Reaction equation

HRID 1510926 reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]([O-:7])=O.[Cl:8][C:9]1[C:15]([O:16][CH2:17][C:18]#[CH:19])=[CH:14][C:12]([NH2:13])=[C:11]([F:20])[CH:10]=1.P(Cl)(Cl)Cl.O.C(=O)(O)[O-].[Na+]>C1(C)C(C)=CC=CC=1>[Cl:8][C:9]1[C:15]([O:16][CH2:17][C:18]#[CH:19])=[CH:14][C:12]([NH:13][C:5](=[O:7])[CH:4]=[N:3][O:2][CH3:1])=[C:11]([F:20])[CH:10]=1

Participants

6

Reactant 4

HCID 24387Phosphorus trichlorideHCID 13272927Benzenamine, 4-chloro-2-fluoro-5-(2-propynyloxy)-HCID 738871062-(Methoxyimino)acetateHCID 86585896Sodium bicarbonate water

Product 1

HCID 86660105N-(4-chloro-2-fluoro-5-propargyloxyphenyl)-2-(methoxyimino)acetamideYield 49.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

0.58 g of the obtained 2-(methoxyimino)acetate was dissolved in 30 ml of xylene and 1.00 g of 4-chloro-2-fluoro-5-propargyloxyaniline was added thereto. 0.17 ml of phosphorus trichloride was then added to the resulting solution and the entire mixture was heated to reflux for 1 hour. After cooling the resulting reaction solution, sodium bicarbonate water was added thereto and the resultant solution was then extracted with ethyl acetate. After washing with saturated saline, the organic layer was dried with anhydrous magnesium sulfate and filtered. The concentrate obtained by evaporating solvents from the filtrate under reduced pressure was washed with a mixed solvent of ether-normal hexane to obtain 0.70 g of N-(4-chloro-2-fluoro-5-propargyloxyphenyl)-2-(methoxyimino)acetamide (yield 49%).

Workup

  1. temperaturethe entire mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperatureAfter cooling
  4. additionwas added
  5. extractionthe resultant solution was then extracted with ethyl acetate
  6. washAfter washing with saturated saline
  7. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customThe concentrate obtained
  10. customby evaporating solvents from the filtrate under reduced pressure
  11. washwas washed with a mixed solvent of ether-normal hexane

Sources & evidence

ORD record
ord-48babf86439c4e47ab488c78faf9b11f
Source dataset
uspto-grants-2012_07
Patent number
US08212050B2

Reaction notes

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