Thionyl Chloride → HCID 18981624, compound
Reaction equation
[CH2:1]([P:3]([CH2:9][O:10][S:11]([C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:21])(=[O:13])=[O:12])(=O)[O:4]C(C)C)[CH3:2].S(Cl)([Cl:24])=O>ClCCCl>[CH2:1]([P:3]([Cl:24])([CH2:9][O:10][S:11]([C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:21])(=[O:13])=[O:12])=[O:4])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A mixture of 20.0 g of O-isopropyl P-ethyl[[2-chloro-6-methylphenyl)sulfonyloxy]methyl]phosphinate (Compound 119), 80 ml of 1,2-dichloroethane and 4.6 ml of thionyl chloride was heated to 50° C. for four hours. 31P NMR analysis of an aliquot of the reaction showed that one third of the starting material was still present so the reaction was heated to 50° C. for 1.5 hours, cooled and let stand at room temperature for 65 hours, heated again to 50° C. for 4 hours and let stand overnight. 31P NMR indicated that starting material was still present so 2 ml of thionyl chloride was added and the reaction was heated to 50° C. for 3.5 hours. The reaction mixture was concentrated under reduced pressure to yield 19.4 g of the desired phosphinoyl chloride which was shown to be 95% pure by 31P NMR. Using the above procedure, the following phosphinoyl chloride of Formula IX was prepared form the indicated compound: P-methyl[[(2-chloro-6isopropylphenyl)sulfonyloxy]methyl]phosphinoyl chloride was prepared from Compound 197 (Example 33).
Workup
- temperaturewas heated to 50° C. for 1.5 hours
- temperaturecooled
- temperatureheated again to 50° C. for 4 hours
- waitlet stand overnight
- additionwas added
- temperaturethe reaction was heated to 50° C. for 3.5 hours
- concentrationThe reaction mixture was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-e5977fe6af0c46abb73acd68a91c6c1f
- Source dataset
- uspto-grants-1993_12
- Patent number
- US05272128
Reaction notes
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