Pyridine → Tris-(tributylammonium) pyrophosphate

HRID 1886506Notes

Reaction equation

HRID 1886506 reaction equation
O.O.O.O.O.O.O.O.O.O.[O-:11][P:12]([O:15][P:16]([O-:19])([O-:18])=[O:17])(=[O:14])[O-:13].[Na+].[Na+].[Na+].[Na+].[CH2:24]([N:28]([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH3:27].N1C=CC=CC=1>O.CN(C)C=O>[O-:13][P:12]([O:15][P:16]([OH:19])([O-:18])=[O:17])(=[O:11])[O-:14].[CH2:33]([NH+:28]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:29][CH2:30][CH2:31][CH3:32])[CH2:34][CH2:35][CH3:36].[CH2:33]([NH+:28]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:29][CH2:30][CH2:31][CH3:32])[CH2:34][CH2:35][CH3:36].[CH2:33]([NH+:28]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:29][CH2:30][CH2:31][CH3:32])[CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7622TributylamineHCID 3084150Sodium pyrophosphate decahydrate

Product 1

HCID 22621555Tris-(tributylammonium) pyrophosphate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent2×

Procedure

Tetrasodium pyrophosphate decahydrate (4.46 g, 10 mmol) was dissolved in the minimum amount of water (about 50 mL) and passed though a column of AG50W X8 resin (100-200 mesh, 4×10 cm bed; a strongly-acidic, cation exchange, polystyrene resin) poured in water. The column was eluted with water and the eluent was collected in an ice-cooled flask until pH of the eluent approached neutrality. Tri-n-butylamine (Aldrich Gold Label, 7.1 mL, 30 mmol) was added to the eluent and the two phases were stirred vigorously until all of the amine dissolved. The resulting solution was lyophilized. The residue was co-evaporated twice with dry pyridine and once with dry dimethylformamide. The residue was dissolved in dry dimethylforamide (10 mL) and the resulting 1.0M solution was stored (for as long as one month) at 0° under argon until used.

Workup

  1. washThe column was eluted with water
  2. customthe eluent was collected in an ice-
  3. temperaturecooled flask until pH of the eluent
  4. dissolutiondissolved
  5. custom(for as long as one month)
  6. customat 0°

Sources & evidence

ORD record
ord-b94a372ab2524d22b8f2d7ff6dd66968
Source dataset
uspto-grants-1992_09
Patent number
US05151507

Reaction notes

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