Hydrochloric Acid → HCID 23323853, compound

HRID 1413825Notes

Reaction equation

HRID 1413825 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 HCl, 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° at 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 portions of methylene chloride
  4. temperatureheated on a steam bath for 0.5 hr
  5. extractionand extracted with three 100-ml portions of methylene chloride
  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-fc74919b4b664592ae8872d40ed9a01b
Source dataset
uspto-grants-1981_02
Patent number
US04251541

Reaction notes

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