Lithium hydride → HCID 178436207, compound

HRID 1732887Notes

Reaction equation

HRID 1732887 reaction equation
I.[NH:2]=[C:3]1[NH:7][CH2:6][CH2:5][NH:4]1.[H-].[Li+].[CH2:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=1[N:19]=[C:20]=[O:21])[CH3:11]>CN(C)C=O>[CH2:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=1[NH:19][C:20]([N:2]=[C:3]1[NH:7][CH2:6][CH2:5][NH:4]1)=[O:21])[CH3:11]

Participants

5

Reactant 3

HCID 62714Lithium hydrideHCID 27364482-Ethyl-6-methylphenyl isocyanateHCID 178506595HCID 178506595, compound

Product 1

HCID 178436207HCID 178436207, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In a manner similar to that previously described, 15.55 grams (0.073 mole) of 2-iminoimidazoline hydroiodide is added dropwise to a dry cooled suspension of 596 milligrams (0.075 mole) of lithium hydride in 30 milliliters of dimethylformamide under an atmosphere of nitrogen. After completion of the addition, the mixture is allowed to warm to room temperature to complete the reaction. Thereafter the mixture is again cooled, a solution of 8.1 grams (0.05 mole) of 2-ethyl-6-methylphenyl isocyanate in 25 milliliters of dry dimethylformamide is added dropwise over a two hour period and thereafter the resulting mixture is stirred overnight while the temperature is allowed to rise to ambient temperatures to obtain a N-(2-ethyl-6-methylphenyl-N'-(2-imidazolidinylidene)urea product. The base product is recovered by procedures similar to that previously described and after recrystallization from methanol-water, a purified base product, m.p. 185°-187° C. is obtained.

Workup

  1. temperaturecooled
  2. additionAfter completion of the addition
  3. customthe reaction
  4. temperatureThereafter the mixture is again cooled

Sources & evidence

ORD record
ord-727d590dbda04da38ccc9636e9ab8e2a
Source dataset
uspto-grants-1980_12
Patent number
US04239768

Reaction notes

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