Sodium hydride → isopropyl N-n-butoxymethyl-2-bromo-4-methyl-5-imidazolecarboxylate

HRID 986345Notes

Reaction equation

[H-].[Na+].[Br:3][C:4]1[NH:5][C:6]([C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])=[C:7]([CH3:9])[N:8]=1.Cl[CH2:17][O:18][CH2:19][CH2:20][CH2:21][CH3:22]>O1CCCC1>[CH2:19]([O:18][CH2:17][N:5]1[C:6]([C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])=[C:7]([CH3:9])[N:8]=[C:4]1[Br:3])[CH2:20][CH2:21][CH3:22]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 293 milligrams (1.22 mM) of sodium hydride in 30 ml of anhydrous tetrahydrofuran was added, in portions, 3 g (1.22 mM) of isopropyl 2-bromo-4-methyl-5-imidazolecarboxylate. The resulting suspension was cooled to 0° C. and 1.5 g (1.22 mM) of chloromethyl-n-butyl ether was added dropwise. The reaction mixture was stirred overnight at room temperature. The precipitated sodium chloride was removed by filtration and concentration of the filtrate in vacuo gave 3.6 g of isopropyl N-n-butoxymethyl-2-bromo-4-methyl-5-imidazolecarboxylate as a golden oil (87%). Subsequent analysis indicated that the 3-isomer/1-isomer ratio was 91/9.

Workup

customThe precipitated sodium chloride was removed by filtration and concentration of the filtrate in vacuo

Sources & evidence

ORD record: ord-89a68d88d12949dab80381831df1a89d
Source dataset: uspto-grants-1987_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04711962

Reaction notes

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