2-Isopropylphenol → Bis(2-isopropylphenyl) chlorothiophosphate

HRID 1647653Notes

Reaction equation

HRID 1647653 reaction equation
[H-].[Na+].[CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])([CH3:5])[CH3:4].[P:13]([Cl:17])(Cl)(Cl)=[S:14]>C1(C)C=CC=CC=1>[P:13]([Cl:17])([O:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH:3]([CH3:5])[CH3:4])([O:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH:3]([CH3:5])[CH3:4])=[S:14]

Participants

5

Reactant 3

HCID 69432-IsopropylphenolHCID 19883Thiophosphoryl chlorideHCID 24758Sodium hydride

Product 1

HCID 54321892Bis(2-isopropylphenyl) chlorothiophosphate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sodium hydride (38.0 g of 80% suspension in mineral oil) was added to a stirred solution of 2-isopropylphenol (139.2 g) and thiophosphoryl chloride (84.5 g) in toluene (500 cm3) at such a rate that the reaction temperature did not rise above 65° C. After stirring for a further 0.5 hr at ambient temperature, the solution was extracted twice with water (250 cm3 portions). separated, dried (MgSO4) and concentrated by distillation of solvents under reduced pressure yielding crude bis(2-isopropylphenyl) chlorothiophosphate, a brown oil (164.2 g); 51P NMR in CDCl3, singlet 53.0 ppm downfield of H3PO4). Of this material, 54.0 g were reacted with ammonia by the procedure of Example 9 yielding crude bis(2-isopropylphenyl)thiophosphoramide) (50.0 g; 31 pNmr, singlet δ=58.8 ppm).

Workup

  1. customdid not rise above 65° C
  2. extractionthe solution was extracted twice with water (250 cm3 portions)
  3. customseparated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated by distillation of solvents under reduced pressure

Sources & evidence

ORD record
ord-05c11efbf35e4df8b369c39fb2b8f48a
Source dataset
uspto-grants-1995_07
Patent number
US05433855

Reaction notes

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