Sodium Iodide → HCID 178469080, compound

HRID 726256Notes

Reaction equation

HRID 726256 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.Cl.Cl[CH2:15][CH2:16][C:17]1[N:18]=[CH:19][NH:20][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O>[CH2:9]([O:8][C:6]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:15][CH2:16][C:17]2[N:18]=[CH:19][NH:20][CH:21]=2)=[CH:12][CH:11]=1)=[O:7])[CH3:10]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 1784785704-(2-chloroethyl)-1H-imidazole hydrochloride

Product 1

HCID 178469080HCID 178469080, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.49 g (9 mmol) of ethyl 4-hydroxybenzoate, 251 mg (1.5 mmol) of 4-(2-chloroethyl)-1H-imidazole hydrochloride, 500 g (3.6 mmol) of potassium carbonate and sodium iodide (catalyst) are stirred at 80° C. for 4 days in 5 ml of dimethylformamide. The reaction mixture is cooled and then filtered. The filtrate is evaporated under reduced pressure to give an oily residue. The excess ethyl 4-hydroxybenzoate is extracted with ether at pH=1. The aqueous solution is evaporated under reduced pressure to give the title compound. The latter is purified by preparative high performance chromatography and converted to the oxalate which, after crystallization from an isopropanol/ether mixture, melts at 160°-164° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered
  3. customThe filtrate is evaporated under reduced pressure
  4. customto give an oily residue
  5. extractionThe excess ethyl 4-hydroxybenzoate is extracted with ether at pH=1
  6. customThe aqueous solution is evaporated under reduced pressure

Sources & evidence

ORD record
ord-62644aa730454384ae074a30387fe78d
Source dataset
uspto-grants-1998_01
Patent number
US05708171

Reaction notes

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