ChemicalBook CAS DataBase List (2-BUTYL-5-CHLORO-1H-IMIDAZOL-4-YL)METHANOL

(2-BUTYL-5-CHLORO-1H-IMIDAZOL-4-YL)METHANOL synthesis

10synthesis methods

Product Name:(2-BUTYL-5-CHLORO-1H-IMIDAZOL-4-YL)METHANOL
CAS Number:79047-41-9
Molecular formula:C8H13ClN2O
Molecular Weight:188.65

123-91-1 Synthesis

123-91-1
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(2-butyl-1H-imidazole-4,5-diyl)dimethanol

136317-69-6
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(2-BUTYL-5-CHLORO-1H-IMIDAZOL-4-YL)METHANOL

79047-41-9
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Yield: 51%

Reaction Conditions:

with N-chloro-succinimide in ethanol

Steps:

1 EXAMPLE 1
EXAMPLE 1 1.45 Grams (10.9 mmol) of an N-chlorosuccinimide was added to a solution consisting of 1.91 g (10.4 mmol) of a 2-butyl-4,5-bis(hydroxymethyl) imidazole, 100 ml of ethanol and 40 ml of 1,4-dioxane maintained at room temperature. The mixture was reacted for 18 hours with stirring and, then, the solvent was distilled off under reduced pressure. The resulting reaction product was washed with water and was recrystallized from acetonitrile to obtain a pale yellowish scale-like crystalline 2-butyl-4- chloro-5-(hydroxymethyl) imidazole in an amount of 1.00 g (yield, 51%). Recrystallization was further effected with acetonitrile to obtain the milk-white crystalline compound in pure form. The thus obtained 2-butyl-4-chloro-5-(hydroxymethyl) imidazole exhibited TLC and spectra as follows: Milk-white crystal, m.p., 141°-147° C. TLC (silica gel-acetone): Rf 0.73 IR(KBr): ν2975, 1598, 1524, 1456, 1392, 1355, 1304, 1284, 1269, 1240, 1222, 1106, 1023, 860, 800, 726, 715 cm^-1

References:

Shikoku Chemicals Corporation US5514811, 1996, A