Phosphoric Acid → HCID 11107274, compound

HRID 1085896Notes

Reaction equation

HRID 1085896 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.[CH2:7](O)[CH2:8][O:9][CH2:10][CH2:11]O.P(=O)(O)(O)O.[OH-].[Na+]>CS(C)=O.C1(C)C=CC=CC=1>[O:9]([CH2:10][CH2:11][N:3]1[CH:4]=[CH:5][N:6]=[C:2]1[CH3:1])[CH2:8][CH2:7][N:3]1[CH:4]=[CH:5][N:6]=[C:2]1[CH3:1]

Participants

7

Reactant 4

HCID 1004Phosphoric AcidHCID 8117Diethylene GlycolHCID 127492-MethylimidazoleHCID 14798Sodium Hydroxide

Product 1

HCID 11107274HCID 11107274, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolvent

Procedure

2-Methyl imidazole (279 g; 3.4 moles), diethylene glycol (159 g; 1.5 mole), toluene (30 g), and 85% phosphoric acid (20 g; 0.17 mole) were charged in a flask equipped with a stirrer, a thermometer, and a distillation column, and the mixture was stirred at 240°~250° C. for 16 hours. Water produced during that time was distilled out by azeotropic distillation with toluene, and after fractionation the toluene was reflexed. The resulting product was incorporated with an aqueous solution of 48% sodium hydroxide (28.8 g; 0.35 mole) and subjected to distillation under reduced pressure of 1 mm Hg at 210°~215° C. to give a fraction of 239 g (yield, 68% based on diethylene glycol). Total amine value: 465 (theoretical value: 479). 'H--NMR (DMSO--d6, δppm)

Workup

  1. customequipped with a stirrer
  2. distillationa thermometer, and a distillation column
  3. customWater produced during that time
  4. distillationwas distilled out by azeotropic distillation with toluene
  5. distillationsubjected to distillation under reduced pressure of 1 mm Hg at 210°~215° C.
  6. customto give
  7. customa fraction of 239 g (yield, 68% based on diethylene glycol)

Sources & evidence

ORD record
ord-0e815c2dd4ef476d8db79915251414d2
Source dataset
uspto-grants-1991_04
Patent number
US05011935

Reaction notes

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