Potassium Carbonate → Dimethyl 1-[6-(2-chloro-4-methoxyphenoxy) hexyl]-4,5-imidazole dicarboxylate

HRID 2210524Notes

Reaction equation

HRID 2210524 reaction equation
[NH:1]1[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:10]([O:12][CH3:13])=[O:11])[N:3]=[CH:2]1.[Cl:14][C:15]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:16]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]SC1SCC(=O)N=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:14][C:15]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:16]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:1]1[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:10]([O:12][CH3:13])=[O:11])[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 768101H-Imidazole-4,5-dicarboxylic acid, 4,5-dimethyl esterHCID 189218352-{[6-(2-Chloro-4-methoxyphenoxy)hexyl]thio}-4,5-dihydrothiazol-4-one

Product 1

HCID 19378829Dimethyl 1-[6-(2-chloro-4-methoxyphenoxy) hexyl]-4,5-imidazole dicarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stir for 24 hours at room temperature 3.7 gm. dimethyl 4,5-imidazole dicarboxylate, 3.7 gm. of the iodide prepared in Examples 2 or 3, 25 ml. DMF and 2.8 gm potassium carbonate. Remove the solvent, extract the residue with methylene chloride, filter, wash methylene chloride fractions with water, elute on a silica column with 100% methylene chloride then 10% methanol/methylene chloride to recover the title compound.

Workup

  1. customRemove the solvent
  2. extractionextract the residue with methylene chloride
  3. filtrationfilter
  4. washwash methylene chloride fractions with water
  5. washelute on a silica column with 100% methylene chloride
  6. custom10% methanol/methylene chloride to recover the title compound

Sources & evidence

ORD record
ord-1280a54c7b2343b2a1f978683ec30e78
Source dataset
uspto-grants-1995_10
Patent number
US05459144

Reaction notes

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