Ethylenediamine → 2-[1-(4,5-Dihydro-1H-imidazol-2-yl)-1-phenylethyl]pyridine

HRID 1679775Notes

Reaction equation

HRID 1679775 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:11])[C:8]([NH2:10])=S.[CH2:18](N)[CH2:19][NH2:20]>>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:8]1[NH:20][CH2:19][CH2:18][N:10]=1)([CH3:11])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 20361728HCID 20361728, compound

Product 1

HCID 2127192-[1-(4,5-Dihydro-1H-imidazol-2-yl)-1-phenylethyl]pyridine

Conditions

Temperature
140 °C

Procedure

Under a nitrogen atmosphere, heat (bath at 140° C) under reflux conditions 2 g. of α-(2-pyridyl)-α-phenylthiopropionamide and 20 ml. of ethylene diamine. Evaporate off the excess diamine, dissolve the residue in benzene, filter, wash, dry and evaporate the benzene solution. Crystallize the residual pale green oil from isopropyl ether to yield 2-[α-(2-pyridyl)α-methylbenzyl]-imidazoline, m.p. 102-103° C. The maleate salt, crystallized from acetonitrile, melts at 156.5°-158° C.

Workup

  1. customEvaporate off the excess diamine
  2. dissolutiondissolve the residue in benzene
  3. filtrationfilter
  4. washwash
  5. customdry
  6. customevaporate the benzene solution
  7. customCrystallize the residual pale green oil from isopropyl ether

Sources & evidence

ORD record
ord-8b86bef29db14746857e4bfe23cc7e62
Source dataset
uspto-grants-1978_03
Patent number
US04081544

Reaction notes

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