Triethylamine → HCID 53872260, compound

HRID 1856103Notes

Reaction equation

HRID 1856103 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([N:5]([CH2:12][P:13]([O:17]Cl)([O:15]Cl)=[O:14])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:4].[C:21]([C:23]1[CH:24]=[C:25]([OH:29])[CH:26]=[CH:27][CH:28]=1)#[N:22].C([N:32]([CH2:35][CH3:36])CC)C>CCOCC>[F:1][C:2]([F:20])([F:19])[C:3]([N:5]([CH2:12][P:13]([O:17][O:29][C:25]1[CH:24]=[CH:23][CH:21]=[C:36]([C:35]#[N:32])[CH:26]=1)([O:15][O:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([C:21]#[N:22])[CH:24]=1)=[O:14])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 133943-CyanophenolHCID 23345669Ethyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate

Product 1

HCID 53872260HCID 53872260, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of ethyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate (4.95 g, 0.015 mole) in ether (100 ml.) was added dropwise with good agitation to a solution of m-cyanophenol (3.57 g, 0.03 mole) and triethylamine (3.03 g, 0.03 mole) in dry ether (50 ml.). The reaction mixture was stirred at room temperature for several hours, then filtered. The filtrate was washed with a 5% solution sodium hydroxide, dried over magnesium sulfate, and concentrated in vacuo to afford ethyl N-trifluoroacetyl-N-(bis(m-cyanophenoxy)phosphonomethyl)glycinate (3.4 g.) as a yellow gum, ND22 =1.5185.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with a 5% solution sodium hydroxide
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-01cae65907ee45ac8dbd32dfcf44273a
Source dataset
uspto-grants-1980_08
Patent number
US04218235

Reaction notes

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