2-(Chloromethyl)-5-methyl-1,2-oxazol-3(2H)-one → HCID 20332918, compound

HRID 1706870Notes

Reaction equation

HRID 1706870 reaction equation
Cl[CH2:2][N:3]1[C:7](=[O:8])[CH:6]=[C:5]([CH3:9])[O:4]1.[P:10]([S-:20])([O:16][CH2:17][CH2:18][CH3:19])([O:12][CH2:13][CH2:14][CH3:15])=[S:11].[K+]>CC(C)=O>[P:10]([S:20][CH2:2][N:3]1[C:7](=[O:8])[CH:6]=[C:5]([CH3:9])[O:4]1)(=[S:11])([O:16][CH2:17][CH2:18][CH3:19])[O:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 203329192-(Chloromethyl)-5-methyl-1,2-oxazol-3(2H)-oneHCID 23678805Potassium O,O-dipropyl dithiophosphate

Product 1

HCID 20332918HCID 20332918, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1.48 g of the 2-chloromethyl-5-methyl-4-isoxazolin-3-one thus obtained in 30 ml of acetone were added 2.52 g of crystalline potassium O,O-di-n-propyl dithiophosphate, and the resulting mixture was then stirred for 1 hour at ambient temperature. The acetone was then evaporated off and the residue was purified by column chromatography through silica gel eluted with a 20:1 by volume mixture of benzene and acetone. There were obtained 2.39 g (73.5% of theory) of O,O-di-n-propyl S-(5-methyl-3-oxo-4-isoxazolin-2-ylmethyl) phosphorodithioate, in the form of a pale yellow oil, n20D =1.5314.

Workup

  1. customThe acetone was then evaporated off
  2. customthe residue was purified by column chromatography through silica gel
  3. washeluted with a 20:1 by volume mixture of benzene and acetone

Sources & evidence

ORD record
ord-ee50bbb9cbb443cdae477a948f326e8d
Source dataset
uspto-grants-1980_06
Patent number
US04209512

Reaction notes

Loading…