Ammonia → HCID 20276873, compound

HRID 1248548Notes

Reaction equation

HRID 1248548 reaction equation
[CH:1]([O:4][P:5]([CH:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:12](O)=[O:13])([O:7][CH:8]([CH3:10])[CH3:9])=[O:6])([CH3:3])[CH3:2].[NH3:25].C(Cl)(Cl)Cl>C(Cl)(=O)C(Cl)=O>[CH:1]([O:4][P:5]([CH:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:12]([NH2:25])=[O:13])([O:7][CH:8]([CH3:10])[CH3:9])=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6212ChloroformHCID 54305009HCID 54305009, compound

Product 1

HCID 20276873HCID 20276873, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 65578Oxalyl chlorideSolvent2×

Conditions

Temperature
35 °C

Procedure

553 g (1.57 moles) of alpha-(diisopropyl phosphono)lauric acid was placed in a 3 liter flask. 791 g (6.28 moles) of distilled oxalyl chloride was carefully added while maintaining the temperature at or slightly below 35° C. (Temperatures much above 35° C. result in oxalyl chloride attack on the phosphonate esters, and too rapid addition results in foaming.) The temperature was maintained at 35° C. for 4 hours, after which I.R. analysis revealed all the acid had converted to the acid chloride. Excess oxalyl chloride was distilled off while maintaining the temperature at 35° C. or below. The product was then diluted with an equal volume of freshly distilled THF and added to a 3 liter flask containing about 1 liter of condensed ammonia. Following a vigorous reaction, the mixture was allowed to stand and warm overnight. Excess ammonia was driven off using a steam bath, and 1 liter of chloroform was added and heated to reflux. The hot chloroform solution was filtered to remove insoluble ammonium chloride and then flash evaporated. The solid residue was dissolved as a 30% solution in pentane, chilled to -78° C. and then placed in a refrigerator. After standing overnight, a crystalline product was collected, dried and ground to a powder. The product weighed 417 g (70% yield) and was pure as verified by TLC and 1H NMR.

Workup

  1. temperaturewhile maintaining the temperature at or slightly below 35° C. (Temperatures much above 35° C.
  2. customresults in foaming
  3. distillationExcess oxalyl chloride was distilled off
  4. temperaturewhile maintaining the temperature at 35° C. or below
  5. additionThe product was then diluted with an equal volume of freshly distilled THF
  6. additionadded to a 3 liter flask
  7. additioncontaining
  8. customabout 1 liter of condensed ammonia
  9. customa vigorous reaction
  10. temperaturewarm overnight
  11. temperatureheated to reflux
  12. filtrationThe hot chloroform solution was filtered
  13. customto remove insoluble ammonium chloride
  14. customflash evaporated
  15. dissolutionThe solid residue was dissolved as a 30% solution in pentane
  16. temperaturechilled to -78° C.
  17. customa crystalline product was collected
  18. customdried

Sources & evidence

ORD record
ord-7d61a5fa68a44d9eb75d1e2a227647a8
Source dataset
uspto-grants-1985_06
Patent number
US04525289

Reaction notes

Loading…