Hydrochloric Acid → HCID 20513928, compound

HRID 1902872Notes

Reaction equation

HRID 1902872 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.[C:23](=O)([O-])[O-].[Na+].[Na+].CI.Cl>CO.CC(C)=O.O1CCOCC1.CCOCC>[ClH:21].[CH2:1]([O:8][N:9]1[CH2:13][CH2:12][N:11]=[C:10]1[N:14]([CH3:23])[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

9

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 178478106HCID 178478106, compound

Product 1

HCID 20513928HCID 20513928, compound

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 16.8 g of 1-(benzyloxy)-2-[(2,6-dichlorophenyl)imino]imidazolidine in 150 ml of dry methanol is treated with 5.83 g of sodium carbonate and 7.81 g of methyl iodide. The mixture is heated to reflux while stirring for 4 hours and then evaporated in vacuo. The residue is partitioned between water and methylene chloride. The organic phase is dried and evaporated. The residual oil is chromatographed on silica gel while eluting with a mixture of chloroform and ethanol (9:1). There is obtained an oil which is dissolved in acetone and treated with hydrogen chloride in dioxane and then with ether until turbidity occurs. The 1-(benzyloxy)-2-(2,6-dichloro-N-methylanilino)-2-imidazoline hydrochloride obtained melts at 185°-186°.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. customevaporated in vacuo
  4. customThe residue is partitioned between water and methylene chloride
  5. customThe organic phase is dried
  6. customevaporated
  7. customThe residual oil is chromatographed on silica gel
  8. washwhile eluting with a mixture of chloroform and ethanol (9:1)
  9. customThere is obtained an oil which

Sources & evidence

ORD record
ord-03e212cdfa9744b09a03d4acffe67b6c
Source dataset
uspto-grants-1982_12
Patent number
US04366160

Reaction notes

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