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Carbon Tetrachloride → 1-Acetyl-1-Methyl-2-Diethoxyphosphoryl Hydrazine

HRID 1395394
Notes
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Reaction equation

HRID 1395394 reaction equation
[C:1]([N:4]([CH3:6])[NH2:5])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C(Cl)(Cl)(Cl)Cl.[CH2:18]([O:20][P:21]([O-:25])[O:22][CH2:23][CH3:24])[CH3:19]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.ClCCl>[C:1]([N:4]([CH3:6])[NH:5][P:21]([O:22][CH2:23][CH3:24])([O:20][CH2:18][CH3:19])=[O:25])(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 5943Carbon TetrachlorideHCID 11430Potassium CarbonateHCID 19051Acetic acid, 1-methylhydrazideHCID 3780918Diethylphosphite

Product 1

HCID 203392921-Acetyl-1-Methyl-2-Diethoxyphosphoryl Hydrazine

Reagents, catalysts & solvents 2

HCID 66133
Benzyl triethylammonium chloride
Catalyst
HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1-acetyl-1-methyl hydrazine (7.84 g., 0.09 mole), potassium carbonate (18.44 g., 0.13 mole) and triethylbenzyl ammonium chloride (0.2 g,) was stirred vigorously at reflux with dichloromethane (90 ml) and carbon tetrachloride (55 ml) for 30 minutes. A solution of diethylphosphite (12.29 g, 0.09 mole) in dichloromethane (18 ml) was then added dropwise to this refluxing mixture and the mixture stirred and refluxed for an additional 20 hours. The mixture was then filtered and the filtrate dried over anhydrous magnesium sulfate. The dried filtrate, then was evaporated down to an oil which was subjected to high vacuum for 2 or 3 hours to yield a liquid product, characterized by proton NMR, infra-red and mass spectroscopy as the subject compound.

Workup

  1. stirringthe mixture stirred
  2. temperaturerefluxed for an additional 20 hours
  3. filtrationThe mixture was then filtered
  4. dry with materialthe filtrate dried over anhydrous magnesium sulfate
  5. customThe dried filtrate, then was evaporated down to an oil which
  6. customwas subjected to high vacuum for 2 or 3 hours
  7. customto yield a liquid product

Sources & evidence

ORD record
ord-a6ef4567212946678b0b7496963aeee6
Source dataset
uspto-grants-1980_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04203932

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes