Methyl iodide → HCID 178502608, compound

HRID 223661Notes

Reaction equation

HRID 223661 reaction equation
Br.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[N:10]=[C:11]1[NH:15][CH2:14][CH2:13][N:12]1[OH:16].[H-].[Na+].[CH3:19]I>CN(C)C=O>[ClH:2].[Cl:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([Cl:2])[C:4]=1[N:10]=[C:11]1[NH:15][CH2:14][CH2:13][N:12]1[O:16][CH3:19]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178419752HCID 178419752, compound

Product 1

HCID 178502608HCID 178502608, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

327 mg. of 2-[(2,6-dichlorophenyl)imino]-1-hydroxyimidazolidine hydrobromide are dissolved in 5 ml. of absolute dimethylformamide, and 90 mg. of sodium hydride are added at 5°. The solution is stirred at room temperature until it becomes clear and is cooled again down to 5° and 1.2 ml. of a 1.0 molar methyl iodide solution in dimethylformamide are added. After 30 minutes, the reaction product is poured onto water and the aqueous phase is extracted twice with ether. The organic extracts are dried and evaporated in vacuo. The residue is dissolved in 1 ml. of acetonitrile, and hydrogen chloride in dioxane is added. The 2-[(2,6-dichlorophenyl)imino]-1-methoxyimidazolidine hydrochloride which has precipitated melts at 228°.

Workup

  1. temperatureis cooled again down to 5° and 1.2 ml
  2. additionthe reaction product is poured onto water
  3. extractionthe aqueous phase is extracted twice with ether
  4. customThe organic extracts are dried
  5. customevaporated in vacuo
  6. dissolutionThe residue is dissolved in 1 ml
  7. additionof acetonitrile, and hydrogen chloride in dioxane is added
  8. customThe 2-[(2,6-dichlorophenyl)imino]-1-methoxyimidazolidine hydrochloride which has precipitated melts at 228°

Sources & evidence

ORD record
ord-ec9325fa69394769badfbe8ed76a84d6
Source dataset
uspto-grants-1982_10
Patent number
US04355033

Reaction notes

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