Dabco → Chlorpyrifos

HRID 328186

Reaktionsgleichung

Reaktionsgleichung von HRID 328186
[P:1](=[S:9])(Cl)([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4].[Cl:10][C:11]1[C:12](C([O-])=O)=[N:13][C:14]([Cl:18])=[C:15]([Cl:17])[CH:16]=1.[Na+].C1N2CCN(CC2)C1.[OH-].[Na+].B([O-])([O-])[O-:34].[Na+].[Na+].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O.C(Cl)Cl>[CH3:4][CH2:3][O:2][P:1]([O:34][C:12]1[C:11]([Cl:10])=[CH:16][C:15]([Cl:17])=[C:14]([Cl:18])[N:13]=1)([O:5][CH2:6][CH3:7])=[S:9]

Komponenten

9

Edukt 5

HCID 9237DabcoHCID 14798Sodium HydroxideHCID 17305O,O-diethyl phosphorochloridothioateHCID 159383boric acid, sodium saltHCID 23699972Sodium 3,5,6-trichloropyridinate

Produkt 1

HCID 2730ChlorpyrifosAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
42 °C

Versuchsvorschrift

O,O-Diethyl phosphorochloridothioate (11.3 g., 0.06 mole) was added dropwise to a stirred mixture of (1) sodium 3,5,6-trichloro-2-pyridinate (13.2 g., .06 mole) in 30 ml. of methylene chloride and 74 ml. of water, (2) 1 mole percent triethylene diamine, (3) 1 mole percent benzyltriethylammonium chloride and (4) a pH buffer consisting of NaOH and sodium borate. The stirred reaction mixture was maintained at 42° C. for 1.5 hours, cooled to room temperature, and the organic phase separated from the aqueous phase. The organic phase was washed once with approximately 30 ml. water and the organic solvent removed under reduced pressure. The title compound was thus obtained in 97 percent yield, based on 100 percent conversion of starting materials. The product was of excellent purity (approximately 99% pure).

Aufarbeitung

  1. customThe stirred reaction mixture
  2. temperaturecooled to room temperature
  3. customthe organic phase separated from the aqueous phase
  4. washThe organic phase was washed once with approximately 30 ml
  5. customwater and the organic solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3cd95343a7914640b2cc6a3c20f9eb5b
Quelldatensatz
uspto-grants-1977_04
Patentnummer
US04016225

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