Sodium Iodide → HCID 178510088, compound

HRID 726254

Reaction equation

HRID 726254 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].Cl.Cl[CH2:12][CH2:13][C:14]1[N:15]=[CH:16][NH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:12][CH2:13][C:14]2[N:15]=[CH:16][NH:17][CH:18]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 1784785704-(2-chloroethyl)-1H-imidazole hydrochloride

Product 1

HCID 178510088HCID 178510088, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

360 mg (3 mmol) of 4-cyanophenol, 251 mg (1.5 mmol) of 4-[2-chloroethyl]imidazole hydrochloride, 500 mg (3.6 mmol) of potassium carbonate and sodium iodide (catalyst) are stirred at 80° C. for 5 days in 5 ml of dimethylformamide. The mixture is cooled and filtered. The filtrate is evaporated under reduced pressure to give an oily residue. The unreacted 4-cyanophenol is precipitated with a methanol/diethyl ether (1/10) mixture. After filtration, the filtrate is evaporated under reduced pressure to give the title compound which is crystallized from a methanol/water (10/3) mixture, M.p.: 181°-183° C.

Workup

  1. temperatureThe mixture is cooled
  2. filtrationfiltered
  3. customThe filtrate is evaporated under reduced pressure
  4. customto give an oily residue
  5. customThe unreacted 4-cyanophenol is precipitated with a methanol/diethyl ether (1/10) mixture
  6. filtrationAfter filtration
  7. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-47b737e856a34a2a813a898a431d3304
Source dataset
uspto-grants-1998_01
Patent number
US05708171

Linked notes

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