3-Allylbenzoylhydrazine → S-ethyl S-hexyl O-{3-[2-(3-allylbenzoylhydrazono)ethyl]phenyl} dithiophosphate

HRID 1105585Notes

Reaction equation

HRID 1105585 reaction equation
[P:1]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH:21]=O)[CH:15]=1)([S:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])([S:3][CH2:4][CH3:5])=[O:2].[CH2:23]([C:26]1[CH:27]=[C:28]([CH:33]=[CH:34][CH:35]=1)[C:29]([NH:31][NH2:32])=[O:30])[CH:24]=[CH2:25]>CO.C(Cl)Cl>[P:1]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH:21]=[N:32][NH:31][C:29](=[O:30])[C:28]2[CH:33]=[CH:34][CH:35]=[C:26]([CH2:23][CH:24]=[CH2:25])[CH:27]=2)[CH:15]=1)([S:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])([S:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 2

HCID 205557863-AllylbenzoylhydrazineHCID 86738192S-ethyl S-hexyl O-(3-formylmethylphenyl) dithiophosphate

Product 1

HCID 86738194S-ethyl S-hexyl O-{3-[2-(3-allylbenzoylhydrazono)ethyl]phenyl} dithiophosphate

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of S-ethyl S-hexyl O-(3-Formylmethylphenyl) dithiophosphate (0.02 mole) in methanol (50 ml) and 3-allylbenzoylhydrazine (0.02 mole) are charged into a glass reaction vessel and the mixture is stirred at room temperature for a period of about 12 hours. After this time the reaction mixture is stripped of methanol under vacuum and the residue is dissolved in methylene chloride (100 ml) and the resulting solution is washed with water (75 ml), with aqueous sodium hydroxide (75 ml; 0.1 N) and again with water (75 ml). The washed solution is then dried over anhydrous magnesium sulfate, filtered and stripped of solvent to yield the desired product S-ethyl S-hexyl O-{3-[2-(3-allylbenzoylhydrazono)ethyl]phenyl} dithiophosphate.

Workup

  1. washthe resulting solution is washed with water (75 ml), with aqueous sodium hydroxide (75 ml; 0.1 N) and again with water (75 ml)
  2. dry with materialThe washed solution is then dried over anhydrous magnesium sulfate
  3. filtrationfiltered

Sources & evidence

ORD record
ord-06a8d1e1afd74dae9c3b65a590ab5b7c
Source dataset
uspto-grants-1982_01
Patent number
US04309422

Reaction notes

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