Phenyl Isothiocyanate → N-(1,3-dimethyl-2-imidazolidinylidene)-N'-phenyl-thiourea

HRID 66562

Reaction equation

HRID 66562 reaction equation
C(N(CC)CC)C.Br.[CH3:9][N:10]1[CH2:14][CH2:13][N:12]([CH3:15])[C:11]1=[NH:16].[C:17]1([N:23]=[C:24]=[S:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)(Cl)Cl>[CH3:9][N:10]1[CH2:14][CH2:13][N:12]([CH3:15])[C:11]1=[N:16][C:24]([NH:23][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[S:25]

Participants

5

Reactant 3

HCID 7673Phenyl IsothiocyanateHCID 8471TriethylamineHCID 134927221,3-Dimethyl-2-imino-imidazolidine hydrobromide

Product 1

HCID 20530303N-(1,3-dimethyl-2-imidazolidinylidene)-N'-phenyl-thiourea

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

30.4 g (0.3 mol) of triethylamine are added to a suspension of 58.2 g (0.3 mol) of 1,3-dimethyl-2-imino-imidazolidine hydrobromide in 470 ml of chloroform, at 5°, with stirring. A solution of 40.6 g (0.3 mol) of phenyl isothiocyanate in 235 ml of chloroform is then added dropwise and the reaction mixture is refluxed for 15 hours. After cooling, it is washed with water, dried over sodium sulfate and evaporated in vacuo. Crude N-(1,3-dimethyl-2-imidazolidinylidene)-N'-phenyl-thiourea is obtained and after recrystallisation from ethanol this melts at 195°-196°.

Workup

  1. temperaturethe reaction mixture is refluxed for 15 hours
  2. temperatureAfter cooling
  3. washit is washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-3610284790264e4e93319b0dd2f35d2c
Source dataset
uspto-grants-1982_08
Patent number
US04342764

Linked notes

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