Dimethylformamide → 2-Butyl-5-chloro-1H-imidazole-4-carbaldehyde

HRID 1756816

Reaction equation

HRID 1756816 reaction equation
[CH2:1]([C:5]1[NH:6][C:7](=[O:10])[CH2:8][N:9]=1)[CH2:2][CH2:3][CH3:4].O=P(Cl)(Cl)[Cl:13].CN(C)[CH:18]=[O:19].[OH-].[Na+]>ClC1C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([C:5]1[NH:6][C:7]([Cl:13])=[C:8]([CH:18]=[O:19])[N:9]=1)[CH2:2][CH2:3][CH3:4].[CH2:1]([C:5]1[NH:6][C:7](=[O:10])[CH2:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 109096542-butyl-3,5-dihydro-4H-imidazol-4-one

Product 2

HCID 551762-Butyl-5-chloro-1H-imidazole-4-carbaldehydeHCID 109096542-butyl-3,5-dihydro-4H-imidazol-4-one

Reagents, catalysts & solvents 2

HCID 7964ChlorobenzeneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

2-n-Butyl-2-imidazolin-5-one (9.81 g, 70 mmol) was added to a solution of phosphoroxychloride (26.83 g, 175 mmol) in chlorobenzene (50 ml) at room temperature. The orange suspension was heated to 100° C. within 5 minutes, and then N,N-dimethylformamide (12.79 g, 175 mmol) was added within 3 minutes. The black mixture was kept for 2 hours at 100° C., cooled to 40° C. and poured on water (84 ml). After addition of ethyl acetate (42 ml), the mixture was stirred for 15 minutes at 26° to 28° C. and then adjusted to pH 7 by addition of 30 percent sodium hydroxide solution (67 ml). The phases were separated, and the aqueous phase was extracted twice with 70 ml of ethyl acetate each. The combined organic phases were dried (MgSO4), filtered and concentrated by evaporation on a Rotavapor. The title compound was obtained in a yield of 8.31 g (64 percent) relative to the 2-n-butyl-2-imidazolin-5-one.

Workup

  1. temperaturecooled to 40° C.
  2. additionpoured on water (84 ml)
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted twice with 70 ml of ethyl acetate each
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation on a Rotavapor

Sources & evidence

ORD record
ord-d85c9d827bb94bcc9444f870b63b5a3a
Source dataset
uspto-grants-1995_08
Patent number
US05442075

Linked notes

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