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ChemicalBook CAS DataBase List 2-Butyl-4-chloro-5-formylimidazole
83857-96-9

2-Butyl-4-chloro-5-formylimidazole synthesis

2synthesis methods
2-Butyl-4-chloro-5-formylimidazole was synthesised as follows: Performing condensation reaction of pentamidine hydrochloride with glyoxal and controlling the pH value of the system in the range of 6.0-7.5; after the reaction terminates, arousing dehydration reaction of the compound of formula III, thereby obtaining 2-butyl-1H-imidazole-5(4H)-ketone; and finally, reacting 2-butyl-1H-imidazole-5(4H)-ketone with N,N-dimethylformamide in the presence of phosphorus oxychloride, thereby obtaining 2-butyl-4-chloro-5-formylimidazole.
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Yield:83857-96-9 12.81 g (86%)

Reaction Conditions:

with manganese dioxide in dichloromethane;

Steps:

1.v (v)

(v) 2-n-Butyl-4-chloro-5-imidazolecarboxaldehyde A stirred mixture of 2-n-butyl-4-chloro-5-hydroxymethylimidazole (15.00 g, 0.0795 mol) and activated manganese dioxide (40.00 g) in 600 ml of methylene chloride was refluxed for 24 h using a water separator. The mixture was filtered hot through a Celite pad. The Celite pad was washed several times with hot methylene chloride. The washings were combined with the filtrate and concentrated in vacuo to give 12.81 g (86%) of the aldehyde as a white solid; mp 97°-98° C.

References:

US5728842,1998,A

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