Diallylamine → ethyl N-trifluoroacetyl-N-(bis(diallylamino)phosphonomethyl)glycinate

HRID 2413064Notes

Reaction equation

HRID 2413064 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].[CH2:21]([NH:24][CH2:25][CH:26]=[CH2:27])[CH:22]=[CH2:23]>O1CCCC1>[F:1][C:2]([F:20])([F:19])[C:3]([N:5]([CH2:12][P:13]([O:17][N:24]([CH2:25][CH:26]=[CH2:27])[CH2:21][CH:22]=[CH2:23])([O:15][N:24]([CH2:25][CH:26]=[CH2:27])[CH2:21][CH:22]=[CH2:23])=[O:14])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:4]

Participants

4

Reactant 2

HCID 31279DiallylamineHCID 23345669Ethyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate

Product 1

HCID 53906450ethyl N-trifluoroacetyl-N-(bis(diallylamino)phosphonomethyl)glycinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate (3.3 g, 0.01 mole) in 25 ml. of tetrahydrofuran was added diallylamine (4.07 g, 0.042 mole) in 50 ml. of tetrahydrofuran. The mixture was stirred at room temperature overnight and was then filtered and the filtrate concentrated in vacuo. The residue was dissolved in ether, washed with water, 10% HCl, water, dried over MgSO4, and concentrated in vacuo. The residue was extracted with petroleum ether, and by concentrating the petroleum ether soluble material, ethyl N-trifluoroacetyl-N-(bis(diallylamino)phosphonomethyl)glycinate was obtained as a light yellow oil, ND =1.4536.

Workup

  1. filtrationwas then filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. dissolutionThe residue was dissolved in ether
  4. washwashed with water, 10% HCl, water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. extractionThe residue was extracted with petroleum ether
  8. concentrationby concentrating the petroleum ether soluble material

Sources & evidence

ORD record
ord-155959e7e80f4ab0907c06a14827cd43
Source dataset
uspto-grants-1985_01
Patent number
US04496389

Reaction notes

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