Ethylenediamine → HCID 20361725, compound

HRID 1580307Notes

Reaction equation

HRID 1580307 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)[C:9]#[N:10])=[CH:4][CH:3]=1.[CH2:16](N)[CH2:17][NH2:18].[S]>>[S:12]1[CH:13]=[CH:14][N:15]=[C:11]1[CH:8]([C:9]1[NH:18][CH2:17][CH2:16][N:10]=1)[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 5362487SulfurHCID 20361795HCID 20361795, compound

Product 1

HCID 20361725HCID 20361725, compound

Procedure

Under a nitrogen atmosphere, heat (110°-115° C), under reflux conditions, a mixture containing 23.5 g. of α-p-chlorphenyl-2-thiazolylacetonitrile, 7 g. of ethylene diamine and 0.2 g. of sulphur for 3 hrs. Extract the black tarry product with 200 ml. of hot benzene, cool and wash the extract with 50 ml. of water. Treat the benzene extract with a cooled solution of 4 ml. of concentrated hydrochloric acid in 25 ml. of water and separate the dark aqueous phase from the benzene. Basify the water extract with sodium carbonate and extract the precipitated oil with two 100 ml. portions of ether. Dry the ether extract and evaporate the ether to obtain 2-[α-(2-thiazolyl)-p-chlorbenzyl]-imidazoline, a viacous red product which is dissolved in acetonitrile and converted to the maleate salt which melts at 145°-147° C.

Workup

  1. temperatureUnder a nitrogen atmosphere, heat (110°-115° C)
  2. additionunder reflux conditions, a mixture containing 23.5 g
  3. extractionExtract the black tarry product with 200 ml
  4. temperatureof hot benzene, cool
  5. washwash the
  6. extractionextract with 50 ml
  7. additionTreat the benzene
  8. extractionextract with a cooled solution of 4 ml
  9. customof water and separate the dark aqueous phase from the benzene
  10. extractionextract with sodium carbonate
  11. extractionextract the precipitated oil with two 100 ml
  12. dry with materialDry the ether
  13. extractionextract
  14. customevaporate the ether

Sources & evidence

ORD record
ord-3e0efdff048740df9b1cf985cd57e37a
Source dataset
uspto-grants-1976_01
Patent number
US03932431

Reaction notes

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