Methyl iodide → 1-(Benzyloxy)-2-[(2,6-dichlorophenyl)imino]-3-methylimidazolidine

HRID 1902873Notes

Reaction equation

HRID 1902873 reaction equation
[CH2:1]([O:8][N:9]1[CH2:13][CH2:12][NH:11][C:10]1=[N:14][C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:25]I>CN(C)C=O.C1(C)C=CC=CC=1>[CH2:1]([O:8][N:9]1[CH2:13][CH2:12][N:11]([CH3:25])[C:10]1=[N:14][C:15]1[C:16]([Cl:22])=[CH:17][CH:18]=[CH:19][C:20]=1[Cl:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178478106HCID 178478106, compound

Product 1

HCID 205138931-(Benzyloxy)-2-[(2,6-dichlorophenyl)imino]-3-methylimidazolidine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

16.8 g of 1-(benzyloxy)-2-[(2,6-dichlorophenyl)imino]-imidazolidine are dissolved in 80 ml of dimethylformamide and treated while stirring at room temperature with 1.44 g of sodium hydride. After 1 hour, there is added dropwise thereto a solution of 4 ml of methyl iodide in 20 ml of toluene. The temperature rises to 48°. After 16 hours, the mixture is poured into ice and extracted with ether. The organic phase is washed successively with water, 15 percent tartaric acid solution and water, dried over magnesium sulfate and evaporated in vacuo. The 1-(benzyloxy)-2-[(2,6-dichlorophenyl)imino]-3-methylimidazolidine obtained is used in the next step without further purification.

Workup

  1. additiontreated
  2. additionthere is added dropwise
  3. customrises to 48°
  4. waitAfter 16 hours
  5. additionthe mixture is poured into ice
  6. extractionextracted with ether
  7. washThe organic phase is washed successively with water, 15 percent tartaric acid solution and water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-51c6fc9731354f0d837d016876089767
Source dataset
uspto-grants-1982_12
Patent number
US04366160

Reaction notes

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