Ethylene Glycol → HCID 70392094, compound

HRID 1722999Notes

Reaction equation

HRID 1722999 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[C:6]([N:13]2[CH2:18][CH2:17][S:16][CH2:15][CH2:14]2)[CH:5]=[C:4]([CH3:19])[N+:3]=1[O-:20].[OH-].[K+].C(O)CO.[ClH:27]>O>[ClH:27].[CH3:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([N:13]2[CH2:14][CH2:15][S:16][CH2:17][CH2:18]2)[CH:5]=[C:4]([CH3:19])[N+:3]=1[O-:20]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13688065HCID 13688065, compound

Product 1

HCID 70392094HCID 70392094, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

38.2 g (0.129 mol) of ethyl 2,6-dimethyl-4-thiomorpholinylpyridine-3-carboxylate 1-oxide(see Table 1, Example 19), 10.6 g (0.189 mol) of solid potassium hydroxide and 100 ml of ethylene glycol were heated at 170° C. for 5 hours. The mixture was then diluted with water, neutralized with 6 N hydrochloric acid, and the water and ethylene glycol were removed by distillation under reduced pressure. The residue was taken up in ethanol, insolubles were removed by filtration, and the solution was boiled with active charcoal, filtered once more and ethanolic HCl was added. The mixture was evaporated to dryness, and the hydrochloride was recrystallized from methanol.

Workup

  1. customthe water and ethylene glycol were removed by distillation under reduced pressure
  2. custominsolubles were removed by filtration
  3. filtrationfiltered once more
  4. additionethanolic HCl was added
  5. customThe mixture was evaporated to dryness
  6. customthe hydrochloride was recrystallized from methanol

Sources & evidence

ORD record
ord-905934552de8484789a1e9d8ce24cdda
Source dataset
uspto-grants-1989_08
Patent number
US04859663

Reaction notes

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