Imidazole → HCID 131710020, compound

HRID 1578449Notes

Reaction equation

HRID 1578449 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.BrC[C:8]1(C2C=CC(Cl)=CC=2Cl)[O:12][CH:11]([CH2:13][O:14]C2C=CC(Cl)=CC=2)C[O:9]1.[I-].[Na+].CN(C)[CH:34]=[O:35].[OH2:37]>>[C:34]([OH:35])(=[O:37])[C:8]([OH:12])=[O:9].[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[C:11]([OH:12])(=[O:35])[C:13]([OH:14])=[O:37].[C:34]([OH:35])(=[O:37])[C:8]([OH:12])=[O:9].[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 5

HCID 795ImidazoleHCID 962WaterHCID 5238Sodium IodideHCID 6228DimethylformamideHCID 20332731HCID 20332731, compound

Product 1

HCID 131710020HCID 131710020, compound

Procedure

A mixture of 6.8 parts of imidazole, 8.5 parts of B -2-(bromomethyl)-4-(p-chlorophenoxymethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane, 2 parts of sodium iodide and 100 parts of dimethylformamide is stirred and refluxed for 36 hours. The reaction mixture is allowed to cool to room temperature and poured into water. The product is extracted twice with benzene. The combined organic layers are washed twice with water, dried and the solvent is removed in vacuo. The residue is purified by column-chromatography over silica gel using chloroform as eluent. The pure fractions are collected and the eluent is evaporated. The residue of B-1-[4-(p-chlorophenoxymethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-2-ylmethyl]-imidazole is converted into the oxalate salt in 4-methyl-2-pentanone: upon the addition of diisopropylether, the salt is precipitated. It is filtered off and crystallized from 4-methyl-2-pentanone, yielding 3.1 parts of trans-1-[4-p-chlorophenoxymethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-2-ylmethyl]-imidazole sesquioxalate; mp. 101°C.

Workup

  1. temperaturerefluxed for 36 hours
  2. extractionThe product is extracted twice with benzene
  3. washThe combined organic layers are washed twice with water
  4. customdried
  5. customthe solvent is removed in vacuo
  6. customThe residue is purified by column-chromatography over silica gel
  7. customThe pure fractions are collected
  8. customthe eluent is evaporated
  9. additionupon the addition of diisopropylether
  10. customthe salt is precipitated
  11. filtrationIt is filtered off
  12. customcrystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-34f3eca7459b43fa92a74eac16eee87e
Source dataset
uspto-grants-1976_02
Patent number
US03936470

Reaction notes

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