Triethylamine → O,O-diethyl isopropyl[[(fluorocarbonyl)methylamino]thio]phosphoramidothioate
Reaction equation
[CH:1]([NH:4][P:5](=[S:12])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8])([CH3:3])[CH3:2].C([N:15]([CH2:18]C)CC)C.ClSN(C)[C:23]([F:25])=[O:24].ON=C([S:31]C)C>O1CCCC1.CCOCC>[CH:1]([N:4]([S:31][NH:15][CH2:18][C:23]([F:25])=[O:24])[P:5](=[S:12])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8])([CH3:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of O,O-diethyl isopropylphosphoramidothioate (14.9 g, 70.8 mmol) and triethylamine (9.8 ml, 70.8 mmol) in tetrahydrofuran (50 ml) is added dropwise over 10 minutes to a solution of N-chlorothio(methyl)carbamoyl fluoride (10.2 g, 70.8 mmol) in tetrahydrofuran (50 ml) cooled in an ice bath. After the addition the mixture is stirred for 1.5 hours at 0°, diluted with ether (200 ml), washed with ice cold water, dried over sodium sulfate and concentrated under reduced pressure. The residue shows identical absorptions in the ir and pmr spectra for γ C=O and N--CH3 as obtained for the yellow oil that is intermediate II1 of Example 1. The crude II1 product is suitable for reaction with methyl N-hydroxyethanimidothioate as in Example 1.
Workup
- temperaturecooled in an ice bath
- additionAfter the addition the mixture
- washwashed with ice cold water
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
- customas obtained for the yellow oil that
Sources & evidence
- ORD record
- ord-d166b7e57f0d4204aee89cbe332ceaae
- Source dataset
- uspto-grants-1984_01
- Patent number
- US04424368
Reaction notes
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