Benzene → HCID 86736900, compound

HRID 2048954Notes

Reaction equation

HRID 2048954 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][N:6]([CH2:13]P(O)=O)[C:7](=[O:12])[C:8]([F:11])([F:10])[F:9])C.[P:18]([Cl:21])(Cl)[Cl:19].[CH:22]1C=CC=C[CH:23]=1>>[CH2:22]([CH:5]([C:4]([OH:3])=[O:17])[N:6]([C:7](=[O:12])[C:8]([F:9])([F:10])[F:11])[CH2:13][P:18]([Cl:21])[Cl:19])[CH3:23]

Participants

4

Reactant 3

HCID 241BenzeneHCID 24387Phosphorus trichlorideHCID 178472840HCID 178472840, compound

Product 1

HCID 86736900HCID 86736900, compound

Procedure

Ethyl-N-(hydroxyphosphinylmethyl)-N-(trifluoroacetyl)glycinate (2.8 g.) was dissolved in benzene and added dropwise to excess phosphorus trichloride with stirring. The solution was filtered and the supernatant liquid decanted and evaporated under vacuum to yield ethyl-N-(trifluoroacetyl)-N-[bis(chloro)phosphinomethyl]glycine as a clear oil. The clear oil was dissolved in tetrahydrofuran and a solution of methane thiol (0.96 g.) and triethylamine (2.05 g.) dissolved in tetrahydrofuran added with stirring. After stirring for an additional one hour, sulfur (0.32 g.) was added and the solution stirred overnight. The reaction mixture was then filtered and the solvent removed under vacuum. The residue was chromatographed on silica gel employing dichloromethane to yield ethyl-N-(trifluoroacetyl)-N-[bis(methanethio)phosphinothioylmethyl]glycine as an oil, ND25 =1.5132 and having the following analysis.

Workup

  1. filtrationThe solution was filtered
  2. customthe supernatant liquid decanted
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-72a8b01a716842d382f44e4384fb3ea0
Source dataset
uspto-grants-1980_04
Patent number
US04195983

Reaction notes

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