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

HRID 1589511Notes

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 (mg) (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 (89%) of the desired product, isopropyl N-n-butoxymethyl-2-bromo-4-methyl-5-imidazolecarboxylate as a golden oil (89% yield).

Workup

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

Sources & evidence

ORD record: ord-d9a1e2668e6846cfb6bd42ea340d366e
Source dataset: uspto-grants-1986_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04571257

Reaction notes

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