Sodium Iodide → HCID 178498267, compound

HRID 744061Notes

Reaction equation

HRID 744061 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.Cl.Cl[CH2:14][CH2:15][C:16]1[N:17]=[CH:18][NH:19][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.C(Cl)(Cl)Cl.CO.C(Cl)(Cl)Cl>[C:6]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:14][CH2:15][C:16]2[N:17]=[CH:18][NH:19][CH:20]=2)=[CH:11][CH:10]=1)([O:8][CH3:9])=[O:7]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 1784785704-(2-chloroethyl)-1H-imidazole hydrochloride

Product 1

HCID 178498267HCID 178498267, compound

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 21584188Chloroform methanolSolvent

Procedure

228 mg (1.5 mmol) of methyl 4-hydroxybenzoate, 251 mg (1.5 mmol) of 4-[2-chloroethyl]-1H-imidazole hydrochloride, 500 mg (3.6 mmol) of potassium carbonate and sodium iodide (catalyst) are stirred at 80° C. for 3 days in 5 ml of dimethylformamide. The reaction mixture is cooled and filtered and the filtrate is evaporated under reduced pressure to give an oily residue which is subjected to column chromatography (using, as first eluent, chloroform and, as second eluent, a 95/5 chloroform/methanol mixture). The product is purified by preparative high performance liquid chromatography and crystallized from water; M.p.: 116°-118° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered
  3. customthe filtrate is evaporated under reduced pressure
  4. customto give an oily residue which
  5. customThe product is purified by preparative high performance liquid chromatography
  6. customcrystallized from water

Sources & evidence

ORD record
ord-54be6b506fbc40d2a88ec19df7180c1d
Source dataset
uspto-grants-1996_09
Patent number
US05559113

Reaction notes

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