Ethylene Glycol → HCID 12698929, compound

HRID 905203Notes

Reaction equation

HRID 905203 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]([CH2:15][N:16]1[CH:20]=[CH:19][N:18]=[CH:17]1)=[O:14])[CH:7]=[CH:6]2)[CH3:2].[CH2:21](O)[CH2:22][OH:23].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>[CH2:21]1[CH2:22][O:23][C:13]([C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([CH2:1][CH3:2])[CH:4]=3)[CH:9]=2)([CH2:15][N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)[O:14]1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 3058920HCID 3058920, compound

Product 1

HCID 12698929HCID 12698929, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.7 g. of 1-[(6-ethyl-2-naphthoyl)methyl]imidazole, 4 ml of ethylene glycol and 1.3 g. of anhydrous p-toluenesulfonic acid 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 sieves and heating is continued for a further day. After cooling, the mixture is treated with 100 ml. of ethyl acetate, neutralized by pouring into excess aqueous potassium carbonate and the organic phase separated, washed with water, dried (MgSO4) and separated to afford 1-[2,2-ethylenedioxy-2-(6-ethyl-2-naphthyl)ethyl]imidazole. This is purified by chromatography on silica gel eluting with 10% methanol/dichloromethane and the hydrochloride salt prepared by dropwise addition of ethereal hydrogen chloride until precipitation is complete. Filtration and recrystallization from acetone/methanol gives 0.38 g. pure hydrochloride, m.p. 251° C.

Workup

  1. additionA mixture of 0.7 g
  2. temperatureunder reflux through a Dean-Stark trap
  3. customThe trap is then replaced by a separatory funnel
  4. additioncontaining 4 A molecular sieves
  5. temperatureheating
  6. waitis continued for a further day
  7. temperatureAfter cooling
  8. additionthe mixture is treated with 100 ml
  9. customthe organic phase separated
  10. washwashed with water
  11. dry with materialdried (MgSO4)
  12. customseparated

Sources & evidence

ORD record
ord-ddb94c7dbb084cdeb35705a409d8f403
Source dataset
uspto-grants-1983_12
Patent number
US04423057

Reaction notes

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