Benzene → O,O-diethyl S-[alpha-(5-methyl-3-oxo-4-isoxazolin-2-yl)benzyl] phosphorodithioate
Reaction equation
Cl[CH:2]([N:9]1[C:13](=[O:14])[CH:12]=[C:11]([CH3:15])[O:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[P:16]([S-:24])([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[S:17].[K+].C1C=CC=CC=1>CC(C)=O>[P:16]([S:24][CH:2]([N:9]1[C:13](=[O:14])[CH:12]=[C:11]([CH3:15])[O:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)(=[S:17])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1.12 g of 2-(α-chlorobenzyl)-5-methyl-4-isoxazolin-3-one in 15 ml of acetone were added 1.12 g of potassium O,O-diethyl dithiophosphate, and the mixture was then shaken for several minutes. After this, 20 ml of benzene were added to the reaction mixture and then most of the acetone was distilled off. After filtering the solution, the solvent was distilled from the filtrate and the remaining yellowish-brown oil was purified by column chromatography through silica gel eluted with a 20:1 by volume mixture of benzene and acetone. There were obtained 1.16 g (62.0% of theory) of O,O-diethyl S-[α-(5-methyl-3-oxo-4-isoxazolin-2-yl)benzyl] phosphorodithioate, in the form of a pale yellow oil, n23D =1.5697.
Workup
- distillationmost of the acetone was distilled off
- filtrationAfter filtering the solution
- distillationthe solvent was distilled from the filtrate
- customthe remaining yellowish-brown oil was purified by column chromatography through silica gel
- washeluted with a 20:1 by volume mixture of benzene and acetone
Sources & evidence
- ORD record
- ord-1a3983915c1941059db83f283768714a
- Source dataset
- uspto-grants-1980_06
- Patent number
- US04209512
Reaction notes
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