(5-Chloro-2-ethyl-1h-imidazol-4-yl)methanol → HCID 178437660, compound

HRID 1874870Notes

Reaction equation

HRID 1874870 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH2:9][CH3:10])[NH:5][C:6]=1[CH2:7][OH:8]>C(Cl)Cl.O1CCOCC1.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[N:3]=[C:4]([CH2:9][CH3:10])[NH:5][C:6]=1[CH:7]=[O:8]

Participants

5

Reactant 1

HCID 10241096(5-Chloro-2-ethyl-1h-imidazol-4-yl)methanol

Product 1

HCID 178437660HCID 178437660, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (4-chloro-2-ethyl-1H-imidazol-5-yl)methanol (1.60 g, 10.0 mmol) and manganese dioxide (5.5 g, 63.3 mmol) in CH2Cl2 (30 mL) and 1,4-dioxane (15 mL) was heated under reflux for 6.5 h. The reaction mixture was cooled to RT, then filtered through Celite, which was washed thoroughly with CH2Cl2. The filtrate was concentrated and dried to provide the title compound (0.763 mg, 48%) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 9.66 (s, 1H), 2.84 (q, 2H), 1.38 (t, 3 H).

Workup

  1. temperatureunder reflux for 6.5 h
  2. filtrationfiltered through Celite, which
  3. washwas washed thoroughly with CH2Cl2
  4. concentrationThe filtrate was concentrated
  5. customdried

Sources & evidence

ORD record
ord-0d4a32eabab741df99c8946045ea0852
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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