Triethylamine → O,O-diethyl isopropyl[[(fluorocarbonyl)methylamino]thio]phosphoramidothioate

HRID 1156502

Reaktionsgleichung

Reaktionsgleichung von HRID 1156502
[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]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 92243Methyl N-hydroxyethanimidothioateHCID 778771Phosphoramidothioic acid, (1-methylethyl)-, O,O-diethyl esterHCID 12922862N-chlorothio(methyl)carbamoyl fluoride

Produkt 1

HCID 86737875O,O-diethyl isopropyl[[(fluorocarbonyl)methylamino]thio]phosphoramidothioate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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 νC=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.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. additionAfter the addition the mixture
  3. washwashed with ice cold water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customas obtained for the yellow oil that

Quellen und Nachweise

ORD-Eintrag
ord-3fc776fce7f74d8bb864eb11f6607529
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04336207

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