2-Butyl-4-chloro-5-(hydroxymethyl)imidazole → HCID 178418251, compound

HRID 1492754Notes

Reaction equation

HRID 1492754 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]([CH2:11][OH:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]>ClCCl.O1CCOCC1.[O-2].[O-2].[Mn+4]>[CH2:1]([C:5]1[NH:6][C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 27356622-Butyl-4-chloro-5-(hydroxymethyl)imidazole

Product 1

HCID 178418251HCID 178418251, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 18626912Dioxane methylene chlorideSolvent

Procedure

A suspension of 2-butyl-4-chloro-1H-imidazole-5-methanol (22.0 g) in dichloromethane:1,4-dioxan (2:1) (690 ml) was treated with manganese dioxide (63.15 g) and the reaction mixture heated at reflux under nitrogen for 3.5 h. The reaction mixture was cooled, filtered and the filtrate evaporated to leave an off-white solid. The residue was triturated with petroleum ether, filtered and dried to give the title compound as a white solid (17.9 g) m.p. 98°-99° C.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux under nitrogen for 3.5 h
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customthe filtrate evaporated
  6. customto leave an off-white solid
  7. customThe residue was triturated with petroleum ether
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-a1bee31fc0e84604a7cc60465f73dd7f
Source dataset
uspto-grants-1994_12
Patent number
US05374646

Reaction notes

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