Toluene → HCID 57371145, compound

HRID 1979888Notes

Reaction equation

HRID 1979888 reaction equation
C([O:4][P:5](=[S:11])([O:7][CH:8]([CH3:10])[CH3:9])[SH:6])(C)C.[O-2].[Zn+2:13].[Zn].[P].[C:16]1(C)[CH:21]=CC=C[CH:17]=1>>[P:5]([O-:4])([O:7][CH:8]([CH3:9])[CH3:10])([S:6][CH:16]([CH3:21])[CH3:17])=[S:11].[Zn+2:13].[CH:16]([S:6][P:5]([O-:4])([O:7][CH:8]([CH3:9])[CH3:10])=[S:11])([CH3:21])[CH3:17]

Participants

6

Reactant 5

HCID 1140TolueneHCID 7876Isopropyl phosphorodithioateHCID 23994ZincHCID 3007857Zinc OxideHCID 5462309Phosphorus

Product 1

HCID 57371145HCID 57371145, compound

Procedure

To a two-liter three-necked flask equipped with a stirrer, nitrogen inlet, and a Dean-Stark trap/condenser was added under nitrogen, 526.5 g (2.25 eq.) of diisopropyl dithiophosphoric acid and about 600 ml toluene. To this solution was added 146.5 g zinc oxide (60% eq. excess) at which point the temperature rose to about 74° C. The reaction mixture was heated to reflux and maintained at reflux for about four hours. A total of about 20 ml of water was collected, after which the reaction mixture was further diluted with 200 ml toluene and filtered hot, two times through Celite. The clear filtrate was stripped in a Rotary-Evaorator under full pump vacuum and a water-bath temperature up to 72° C. The product obtained weighed 592.3 g and was a soft, white, crystalline solid-% zinc=14.00, % phosphorus=13.83.

Workup

  1. customTo a two-liter three-necked flask equipped with a stirrer, nitrogen inlet
  2. additiona Dean-Stark trap/condenser was added under nitrogen
  3. customrose to about 74° C
  4. temperatureThe reaction mixture was heated
  5. temperatureto reflux
  6. temperaturemaintained
  7. temperatureat reflux for about four hours
  8. customA total of about 20 ml of water was collected
  9. additionafter which the reaction mixture was further diluted with 200 ml toluene
  10. filtrationfiltered hot
  11. customwas stripped in a Rotary-Evaorator under full pump vacuum and a water-bath temperature up to 72° C
  12. customThe product obtained

Sources & evidence

ORD record
ord-3ea76566cec14aee8c415f39fa208439
Source dataset
uspto-grants-1984_11
Patent number
US04483775

Reaction notes

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