Diethyl chlorophosphate → HCID 86750859, compound

HRID 1781123Notes

Reaction equation

HRID 1781123 reaction equation
[NH+]12CC[NH+](CC1)CC2.[F:9][B-:10]([F:13])([F:12])[F:11].F[B-](F)(F)F.[CH2:19]([C:21]1([CH2:34][CH3:35])[CH2:26][N+:25]2(P(O)(O)=O)[CH2:27][CH2:28][N+:22]1(F)[CH2:23][CH2:24]2)[CH3:20].[P:36](Cl)([O:41]CC)([O:38]CC)=[O:37].F[B-](F)(F)F.[Na+]>C1COCC1.C(#N)C>[F:9][B-:10]([F:13])([F:12])[F:11].[CH2:34]([C:21]1([CH2:19][CH3:20])[CH2:26][N:25]2[CH2:27][CH2:28][N+:22]1([P:36]([OH:38])([OH:41])=[O:37])[CH2:23][CH2:24]2)[CH3:35]

Participants

6

Reactant 3

HCID 13139Diethyl chlorophosphateHCID 4343483Sodium TetrafluoroborateHCID 86750861HCID 86750861, compound

Product 1

HCID 86750859HCID 86750859, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diethyl 1-Fluoro-4-phosphono-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) 1,4-Diazoniabicyclo[2.2.2]octane (11 g, 10 mmol) in THF (100 mL) is reacted with diethyl chlorophosphate (17.3 g, 10 mmol) until the reaction is complete by TLC. The reaction is evaporated, diluted with acetonitrile (100 mL) and sodium tetrafluoroborate (40 g, 20 mmol) added. The solution is stirred overnight at room temperature and then filtered to remove all undissolved salts. The filtrate is evaporated to afford diethyl- 1-phosphono-4-aza-1-azoniabicyclo[2.2.2]octane tetrafluoroborate.

Workup

  1. customThe reaction is evaporated
  2. additionadded
  3. filtrationfiltered
  4. customto remove all undissolved salts
  5. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-aa05a8bb5ab643cdbd1c7d8827e3a981
Source dataset
uspto-grants-1997_05
Patent number
US05631372

Reaction notes

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