Ethylene Glycol → HCID 12698929, compound

HRID 1277429Notes

Reaction equation

HRID 1277429 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. Thetrap is the replaced by a separatory funnel containing 4 A molecular sievesand 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 evaporated 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. customreplaced by a separatory funnel
  4. additioncontaining 4 A molecular sievesand
  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. customevaporated

Sources & evidence

ORD record
ord-3819fd0ea1344127a9231261af447dd1
Source dataset
uspto-grants-1981_07
Patent number
US04277486

Reaction notes

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