Ethylenediamine → 2-[(3,4-dihydro-1-methyl-2-naphthalenyl)methyl]-4,5-dihydro-1H-imidazole

HRID 1719560Notes

Reaction equation

HRID 1719560 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]=1[CH2:12][C:13]#[N:14].[CH2:15](N)[CH2:16][NH2:17]>C(=S)=S>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]=1[CH2:12][C:13]1[NH:14][CH2:15][CH2:16][N:17]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 134914693,4-Dihydro-1-methyl-2-naphthaleneacetonitrile

Product 1

HCID 134914702-[(3,4-dihydro-1-methyl-2-naphthalenyl)methyl]-4,5-dihydro-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 60 g (0.33 mole) of 3,4-dihydro-1-methyl-2-naphthaleneacetonitrile and 30 ml of ethylenediamine was added 3 ml of carbon disulfide. The reaction mixture was stirred under nitrogen and heated in an oil bath at 120° C. for 21 hours, and then cooled to room temperature and concentrated in vacuo to remove volatile substances. The solid material was collected, dissolved in 600 ml of chloroform and dried over anhydrous magnesium sulfate. The solvent was removed, and the residue was triturated with ether and dissolved in ethanol. The ethanol solution was acidified with ethanolic hydrogen chloride and ether was added until the solution became cloudy. The solid product which crystallized was collected and dried in vacuo to give 28.7 g of 2-[(3,4-dihydro-1-methyl-2-naphthalenyl)methyl]-4,5-dihydro-1H-imidazole in the form of its mono-hydrochloride salt, m.p. 223°-224° C. A recrystallization from the same solvent mixture gave a sample with m.p. 226°-229° C.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customto remove volatile substances
  4. customThe solid material was collected
  5. dissolutiondissolved in 600 ml of chloroform
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed
  8. customthe residue was triturated with ether
  9. dissolutiondissolved in ethanol
  10. additionwas added until the solution
  11. customThe solid product which crystallized
  12. customwas collected
  13. customdried in vacuo

Sources & evidence

ORD record
ord-4857f0048f64460d851d70240f4e5f5b
Source dataset
uspto-grants-1985_09
Patent number
US04540705

Reaction notes

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