Hydrochloric Acid → HCID 23323853, compound

HRID 1381214Notes

Reaction equation

HRID 1381214 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][CH:5]=[CH:4]1)[CH3:2].Cl.ClCl.[C:11]([O-:16])(=[O:15])[C:12]([O-:14])=[O:13]>O>[C:11]([OH:16])(=[O:15])[C:12]([OH:14])=[O:13].[CH2:1]([N:3]1[CH2:7][CH:6]2[O:13][CH:5]2[CH2:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24526ChlorineHCID 71081OxalateHCID 17965882HCID 17965882, compound

Product 1

HCID 23323853HCID 23323853, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 61 g. (0.63 mole) of 1-ethylpyrroline, 50 ml. of concentrated aqueous hydrochloric acid and 600 ml. of water was treated with chlorine gas for 2.5 hr. The mixture was filtered through cotton and the filtrate was washed with two 100-ml. portions of methylene chloride. The aqueous layer was made basic with 20% sodium hydroxide, heated on a steam bath for 0.5 hr. and extracted with three 100-ml. portions of methylene chloride. The combined extracts were dried over anhydrous sodium sulfate and concentrated and the residue vacuum distilled to give 39.4 g. (56%) of the epoxide as a clear oil (b.p. 75°-90° @28 mm.). The epoxide was converted to the oxalate and the salt was recrystallized from absolute ethanol to give white needles, m.p. 142°-4° d.

Workup

  1. additionA mixture of 61 g
  2. filtrationThe mixture was filtered through cotton
  3. washthe filtrate was washed with two 100-ml
  4. temperatureheated on a steam bath for 0.5 hr
  5. extractionand extracted with three 100-ml
  6. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. distillationthe residue vacuum distilled
  9. customto give 39.4 g
  10. customthe salt was recrystallized from absolute ethanol
  11. customto give white needles, m.p. 142°-4°

Sources & evidence

ORD record
ord-ab26a87e71ee4a4ab23b7ba3092a1604
Source dataset
uspto-grants-1986_04
Patent number
US04585785

Reaction notes

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