Ethylene Glycol → HCID 13883909, compound

HRID 231117Notes

Reaction equation

HRID 231117 reaction equation
[Cl:1][C:2]1[C:3]([NH:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH:20]=[O:21])=[CH:15][C:14]=2[CH3:22])=[N:4][CH:5]=[N:6][C:7]=1[CH3:8].[CH2:23](O)[CH2:24][OH:25].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([NH:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH:20]3[O:25][CH2:24][CH2:23][O:21]3)=[CH:15][C:14]=2[CH3:22])=[N:4][CH:5]=[N:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 13883908HCID 13883908, compound

Product 1

HCID 13883909HCID 13883909, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10.0 g of 5-chloro-4-[2-(4-formylmethyl-2-methylphenoxy)ethylamino]-6-methylpyrimidine and 3.0 g of ethylene glycol were dissolved in 300 ml of toluene. A small amount of p-toluenesulfonic acid was added to the solution, and the reaction vessel was equipped with a device for quantitatively determining water. The mixture was then heated under reflux for 8 hours. At the end of this time, the reaction mixture was washed with water and dried over anhydrous sodium sulfate. Toluene was removed by distillation under reduced pressure and the oily product thus obtained was subjected to column chromatography (Wakogel C-200, eluted with a 2:1 by volume mixture of toluene and ethyl acetate) to isolate the product and give 7.9 g of the title compound as a colorless oily liquid, n23.4 =1.5730.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 8 hours
  3. washAt the end of this time, the reaction mixture was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customToluene was removed by distillation under reduced pressure
  6. customthe oily product thus obtained
  7. washeluted with a 2:1 by volume mixture of toluene and ethyl acetate)
  8. customto isolate the product

Sources & evidence

ORD record
ord-0acfe4a309dd4b4ead7fd27a489463fc
Source dataset
uspto-grants-1989_07
Patent number
US04845097

Reaction notes

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