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ChemicalBook CAS DataBase List 1-Methylimidazole

1-Methylimidazole synthesis

8synthesis methods
1-Methylimidazole is prepared mainly by two routes industrially. The main one is acid-catalysed methylation of imidazole by methanol. The second method involves the Radziszewski reaction from glyoxal, formaldehyde, and a mixture of ammonia and methylamine.
(CHO)2 + CH2O + CH3NH2 + NH3 → H2C2N(NCH3)CH + 3 H2O
The compound can be synthesized on a laboratory scale by methylation of imidazole at the pyridine-like nitrogen and subsequent deprotonation. Similarly, 1-methylimidazole may be synthesized by first deprotonating imidazole to form a sodium salt followed by methylation.
H2C2N(NH)CH + CH3I → [H2C2(NH)(NCH3)CH]I
[H2C2(NH)(NCH3)CH]I + NaOH → H2C2N(NCH3)CH + H2O + NaI
-

Yield:616-47-7 98.5%

Reaction Conditions:

with sodium methylate

Steps:

36

Lower layer separated in Example 1 was added with 20.84 g (0.521 moles) of sodium hydroxide at room temperature, followed by stirring for 1 hour. 1- Methylimidazole was recovered (recovery 97.6%) by distilling the remaining solution at a reduced pressure after the produced NaCl was filtered; 1-Methy limidazole was recovered by following the same procedure as described in Example 31 except by using sodium methoxide (NaOCHs) instead of sodium hydroxide, and the recovery was 98.5%.

References:

WO2008/1985,2008,A1 Location in patent:Page/Page column 11

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