Phenylhydrazine → ethyl N-trifluoroacetyl-N-(bis(phenylhydrazino)phosphonomethyl)glycinate

HRID 223311Notes

Reaction equation

HRID 223311 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:9][C:10]([F:28])([F:27])[C:11]([N:13]([CH2:20][P:21]([O:25]Cl)([O:23]Cl)=[O:22])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:12]>CCOCC>[F:9][C:10]([F:28])([F:27])[C:11]([N:13]([CH2:20][P:21]([O:25][NH:8][NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([O:23][NH:8][NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:22])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:12]

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 23345669Ethyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate

Product 1

HCID 53935690ethyl N-trifluoroacetyl-N-(bis(phenylhydrazino)phosphonomethyl)glycinateYield 11.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of phenylhydrazine (4.5 g, 0.0423 mole) in 40 ml. of ether was added dropwise with good stirring ethyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate (3.3 g, 0.01 mole) dissolved in ether. The reaction was stirred at room temperature for two hours, then filtered and the filtrate concentrated in vacuo to give a gum-solid. This was triturated with petroleum ether, then ether. The ether insoluble solid was washed with water to give ethyl N-trifluoroacetyl-N-(bis(phenylhydrazino)phosphonomethyl)glycinate (0.6 g), m.p. 113°-116° C. (glass), 143°-145° C. with decomposition.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated in vacuo
  3. customto give a gum-solid
  4. customThis was triturated with petroleum ether
  5. washThe ether insoluble solid was washed with water

Sources & evidence

ORD record
ord-8bdf5247c7324d0eb7a7264309ed99b1
Source dataset
uspto-grants-1982_10
Patent number
US04353731

Reaction notes

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