(4-chloro-2-propyl-1H-imidazol-5-yl)methanol → 1H-Imidazole-4-carboxaldehyde, 5-chloro-2-propyl-

HRID 1874876Notes

Reaction equation

HRID 1874876 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH2:9][CH2:10][CH3:11])[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][CH2:10][CH3:11])[NH:5][C:6]=1[CH:7]=[O:8]

Participants

5

Reactant 1

HCID 10374924(4-chloro-2-propyl-1H-imidazol-5-yl)methanol

Product 1

HCID 97939751H-Imidazole-4-carboxaldehyde, 5-chloro-2-propyl-Yield 59.1%

Reagents, catalysts & solvents 3

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

Procedure

A solution of (4-chloro-2-propyl-1H-imidazol-5-yl)methanol (0.927 g, 5.3 mmol) and manganese dioxide (2 g, 23.0 mmol) in CH2Cl2 (12 mL) and 1,4-dioxane (6 mL) was heated under reflux for 6 h. The reaction mixture was cooled to RT, then filtered through celite, washing thoroughly with CH2Cl2. The filtrate was concentrated and dried to provide the title compound (0.541 g, 59%) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 11.61 (br. s., 1H), 9.63 (s, 1H), 2.80 (t, 2H), 1.83 (sex, 2 H), 0.99 (t, 3H). ES-LCMS: m/z 173.0 (M+1).

Workup

  1. temperatureunder reflux for 6 h
  2. filtrationfiltered through celite
  3. washwashing thoroughly with CH2Cl2
  4. concentrationThe filtrate was concentrated
  5. customdried

Sources & evidence

ORD record
ord-7026188fd6f5468fab746336b668eb2c
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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