Triethylene Glycol → HCID 17967851, compound

HRID 1587699Notes

Reaction equation

HRID 1587699 reaction equation
[C:1]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].NN.[OH-].[K+].C(O)COCCOCCO>O>[CH2:1]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 8172Triethylene GlycolHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 19756112HCID 19756112, compound

Product 1

HCID 17967851HCID 17967851, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 12.2 g (49 mmol) of 3-n-undecanoylpyridine, 7.60 g (0.15 mol) of hydrazine.monohydrate and 5.60 g (0.10 mol) of potassium hydroxide and 50 ml of triethylene glycol was heated at 110° to 125° C. for one hour, and further, at 180° to 185° C. for 6 hours. After cooling, 200 ml of water was added, and the mixture was extracted with diethyl ether, and after washing with water, the extract was dried with anhydrous sodium sulfate. After concentration under a reduced pressure, the residue was purified by distillation under a reduced pressure to obtain 11.0 g of the desired product (yield 95.6%).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with diethyl ether
  3. washafter washing with water
  4. dry with materialthe extract was dried with anhydrous sodium sulfate
  5. concentrationAfter concentration under a reduced pressure
  6. distillationthe residue was purified by distillation under a reduced pressure

Sources & evidence

ORD record
ord-e8840890ce9343c6859b5a4b5d7e7146
Source dataset
uspto-grants-1993_06
Patent number
US05219847

Reaction notes

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