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

HRID 1580308Notes

Reaction equation

HRID 1580308 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-78265b2d5bae478199733e2c6edb96ec
Source dataset
uspto-grants-1976_01
Patent number
US03932431

Reaction notes

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