Hydrochloric Acid → 1-(2-Methoxyphenyl)-2-imidazolidinethione

HRID 1531843Notes

Reaction equation

HRID 1531843 reaction equation
C(O[CH:4](OCC)[CH2:5][NH2:6])C.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]=[C:19]=[S:20].Cl>C1(C)C=CC=CC=1>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]1[CH2:4][CH2:5][NH:6][C:19]1=[S:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 695242,2-DiethoxyethylamineHCID 5205992-Methoxyphenyl Isothiocyanate

Product 1

HCID 570963221-(2-Methoxyphenyl)-2-imidazolidinethioneYield 60.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

8.8 ml (0.065 mol) of aminoacetaldehyde-diethylacetal diluted in 15 ml of toluene are added, under nitrogen, to a solution of 10 g (0.065 mol) of 2-methoxyphenylisothiocyanate in 105 ml of toluene. The reaction mixture is stirred for 1 h 30 min at room temperature. 2.75 ml (0.030 mol) of hydrochloric acid at 35% are added and the mixture is stirred for 2 hours under reflux. The mixture is concentrated and water is added and the precipitate is triturated. The product is drained, washed with an ether/n-heptane mixture and dried over P2O5 overnight. 8.18 g of 1-(2-methoxyphenyl)imidazoline-2-thione are thus obtained.

Workup

  1. stirringthe mixture is stirred for 2 hours
  2. temperatureunder reflux
  3. concentrationThe mixture is concentrated
  4. additionwater is added
  5. customthe precipitate is triturated
  6. washwashed with an ether/n-heptane mixture
  7. dry with materialdried over P2O5 overnight

Sources & evidence

ORD record
ord-cafc4451c79a4dfda45ea124cf9987fa
Source dataset
uspto-grants-2001_03
Patent number
US06200991B1

Reaction notes

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