Water → Phosphorothioate

HRID 1105575Notes

Reaction equation

HRID 1105575 reaction equation
[P:1]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH:17]=O)([S:6][CH2:7][CH2:8][CH3:9])([O:3][CH2:4][CH3:5])=[O:2].[C:19]([NH:27][NH2:28])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CO>[P:1]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH:17]=[N:28][NH:27][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([S:6][CH2:7][CH2:8][CH3:9])([O:3][CH2:4][CH3:5])=[O:2].[P:1]([O-:10])([O-:3])([O-:2])=[S:6]

Participants

6

Reactant 3

HCID 962WaterHCID 11955BenzoylhydrazineHCID 12814299HCID 12814299, compound

Product 2

HCID 167253PhosphorothioateHCID 54212030HCID 54212030, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of O-ethyl S-propyl O-(2-formylphenyl) thiophosphate (4.1 grams; 0.0142 mole) in methanol (50 ml) was charged into a glass reaction vessel equipped with a mechanical stirrer. Benzoylhydrazine (1.939 grams; 0.0142 mole) was added and the reaction mixture was stirred at room temperature overnight. After this time water was added to the reaction mixture until it became cloudy. The mixture was then heated on a steam bath until it became clear again. The reaction mixture was then cooled in an ice bath resulting in the formation of a solid precipitate. The precipitate was recovered by filtration and washed with isopropyl ether. The washed product was then air dried for 15 minutes and thereafter dried overnight in a vacuum oven to yield the desired product O-ethyl S-propyl O-[2-benzoylhydrazonomethyl)phenyl] thiophosphate as a white powder.

Workup

  1. customequipped with a mechanical stirrer
  2. temperatureThe mixture was then heated on a steam bath until it
  3. temperatureThe reaction mixture was then cooled in an ice bath
  4. customresulting in the formation of a solid precipitate
  5. filtrationThe precipitate was recovered by filtration
  6. washwashed with isopropyl ether
  7. customair dried for 15 minutes
  8. customdried overnight in a vacuum oven

Sources & evidence

ORD record
ord-cfa2b2044c9c41249c900e42f5ef3ef5
Source dataset
uspto-grants-1982_01
Patent number
US04309422

Reaction notes

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