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

HRID 232103

Reaction equation

HRID 232103 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 and 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-44b726412bb246759a6c6e8ff26056bc
Source dataset
uspto-grants-1989_07
Patent number
US04851423

Linked notes

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