Ethanol → HCID 53924229, compound

HRID 1105578Notes

Reaction equation

HRID 1105578 reaction equation
[P:1]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=O)[CH:12]=1)([S:6][CH2:7][CH2:8][CH3:9])([O:3][CH2:4][CH3:5])=[O:2].C(O)C.[C:22]([NH:30][NH2:31])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CO>C(Cl)Cl>[P:1]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=[N:31][NH:30][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:12]=1)([S:6][CH2:7][CH2:8][CH3:9])([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 887MethanolHCID 11955BenzoylhydrazineHCID 53791799HCID 53791799, compound

Product 1

HCID 53924229HCID 53924229, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

O-Ethyl S-propyl O-(3-formylphenyl) thiophosphate (6.0 grams; 0.016 mole), ethanol (100 ml) and benzoylhydrazine (2.18 grams; 0.016 mole) were charged into a glass reaction vessel equipped with a mechanical stirrer. The reaction mixture was stirred at room temperature overnight. After this time the reaction mixture was stripped of methanol leaving an orange oil. This oil was dissolved in methylene chloride and the resulting solution was washed twice with water (100 ml), twice with aqueous sodium hydroxide (50 ml; 0.1 N) and again twice with water (100 ml). The washed solution was then dried over anhydrous magnesium sulfate and was stripped of solvent under vacuum to yield the desired product O-ethyl S-propyl O-[3-(benzoylhydrazonomethyl)phenyl]thiophosphate as a viscous orange oil.

Workup

  1. customequipped with a mechanical stirrer
  2. washthe resulting solution was washed twice with water (100 ml), twice with aqueous sodium hydroxide (50 ml; 0.1 N) and again twice with water (100 ml)
  3. dry with materialThe washed solution was then dried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-74f1e6e3a0034417b3bf7bdc0b0a2b4d
Source dataset
uspto-grants-1982_01
Patent number
US04309422

Reaction notes

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