Bis(2-chloroethyl) ether → HCID 20356333, compound

HRID 371751Notes

Reaction equation

HRID 371751 reaction equation
[NH2:1][C:2]12[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.[CH2:11]([O:14][CH2:15][CH2:16]Cl)[CH2:12][Cl:13]>>[ClH:13].[CH3:9][C:8]1([CH3:10])[C:2]2([N:1]3[CH2:16][CH2:15][O:14][CH2:11][CH2:12]3)[CH2:7][CH2:6][CH:5]1[CH2:4][CH2:3]2

Participants

3

Reactant 2

HCID 8115Bis(2-chloroethyl) etherHCID 20356317HCID 20356317, compound

Product 1

HCID 20356333HCID 20356333, compound

Procedure

A stirred mixture of 1-amino-7,7-dimethylnorbornane (0.7 gm) potassium carbonate (0.77 gm) and 2,2'-dichlorodiethyl ether (3 ml) was heated at 130° for 2 hrs. The reaction mixture was then cooled and partitioned between ether and 2 N hydrochloric acid solution. The aqueous layer was separated basified and extracted into ether. The organic layer was dried, and evaporated. The residue (0.8 gm) after purification by chromatography was dissolved in dry ether and treated with hydrogen chloride to give the title compound (0.33 gm) m.p. 243° to 246°.

Workup

  1. temperaturewas heated at 130° for 2 hrs
  2. temperatureThe reaction mixture was then cooled
  3. custompartitioned between ether and 2 N hydrochloric acid solution
  4. customThe aqueous layer was separated
  5. extractionextracted into ether
  6. customThe organic layer was dried
  7. customevaporated
  8. customThe residue (0.8 gm) after purification by chromatography
  9. dissolutionwas dissolved in dry ether
  10. additiontreated with hydrogen chloride

Sources & evidence

ORD record
ord-bd8d6aacfc9e438c840e3c9220de44da
Source dataset
uspto-grants-1978_05
Patent number
US04087551

Reaction notes

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