Ethylene Glycol → 1-[2,2-Ethylenedioxy-2-(2-naphthyl)ethyl]imidazole

HRID 26540

Reaction equation

HRID 26540 reaction equation
Cl.[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)=[O:13].[CH2:20](O)[CH2:21][OH:22].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH2:20]1[CH2:21][O:22][C:12]([C:3]2[CH:4]=[CH:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:2]=2)([CH2:14][N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)[O:13]1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 11430Potassium CarbonateHCID 51199Nafimidone monohydrochlorideHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 30541231-[2,2-Ethylenedioxy-2-(2-naphthyl)ethyl]imidazole

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5.45 g. of 1-(2-naphthoylmethyl)imidazole hydrochloride, 2.49 g. ethylene glycol and 7.6 g. p-toluenesulfonic acid monohydrate in 50 ml. of toluene is heated overnight under reflux through a Dean-Stark trap. The trap is then replaced by a separatory funnel containing 4 A molecular seives and heating is continued for a further day. After cooling, the mixture is treated with 200 ml. of ethyl acetate, neutralized by pouring into excess aqueous potassium carbonate and the organic phase separated and dried (MgSO4) to afford a solution of 1-[2,2-ethylenedioxy-2-(2-naphthyl)ethyl]imidazole. The hydrochloride salt is prepared by dropwise addition of ethereal hydrogen chloride until precipitation is complete. Filtration and recrystallization from acetone/methanol gives 3.9 g. pure hydrochloride. m.p. 269°-270° C.

Workup

  1. additionA mixture of 5.45 g
  2. temperatureunder reflux through a Dean-Stark trap
  3. customThe trap is then replaced by a separatory funnel
  4. additioncontaining 4 A molecular seives
  5. temperatureheating
  6. waitis continued for a further day
  7. temperatureAfter cooling
  8. additionthe mixture is treated with 200 ml
  9. customthe organic phase separated
  10. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-f5f7466ae81b4ad3bd899d47583d00e1
Source dataset
uspto-grants-1979_04
Patent number
US04150153

Linked notes

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