Dabco → Chlorpyrifos

HRID 372668

Reaction equation

HRID 372668 reaction equation
[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]

Participants

9

Reactant 5

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

Product 1

HCID 2730ChlorpyrifosYield 97%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
42 °C

Procedure

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., 0.06 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).

Workup

  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

Sources & evidence

ORD record
ord-e2c5fe5102bb47d589f53de7466bdb0a
Source dataset
uspto-grants-1978_05
Patent number
US04092312

Linked notes

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