Acetic Acid → HCID 14257101, compound

HRID 622114Notes

Reaction equation

HRID 622114 reaction equation
[C:1]([CH:6]=[CH:7][C:8]1[N:12]([CH3:13])[C:11]([S:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[N:10][C:9]=1[CH3:24])([O:3][CH2:4][CH3:5])=[O:2].N(C([O-])=O)=NC([O-])=O.[K+].[K+].C(O)(=O)C>CO>[C:1]([CH2:6][CH2:7][C:8]1[N:12]([CH3:13])[C:11]([S:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[N:10][C:9]=1[CH3:24])([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6096233Potassium diazene-1,2-dicarboxylateHCID 54335975HCID 54335975, compound

Product 1

HCID 14257101HCID 14257101, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-[2-(carbethoxy)ethenyl]-1,4-dimethyl-2-(4-methoxybenzylthio)imidazole (600 mg, 1.7 mmole) and potassium azodicarboxylate (29 g, 0.17 mole) in methanol (50 ml) was stirred and treated with acetic acid (7 g, 0.12 mole). The mixture was concentrated in vacuo, partitioned between methylene chloride and 5% aqueous sodium carbonate, and the organic phase was concentrated in vacuo. The residue was chromatographed on silica gel eluted with ethyl acetate to give 5-[2-(carbethoxy)ethyl]-1,4-dimethyl-2-(4-methoxybenzylthio)imidazole (mp 63° C.).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompartitioned between methylene chloride and 5% aqueous sodium carbonate
  3. concentrationthe organic phase was concentrated in vacuo
  4. customThe residue was chromatographed on silica gel
  5. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-3e6e8d5b7af64071b1bcfc2688ee6149
Source dataset
uspto-grants-1988_09
Patent number
US04769386

Reaction notes

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