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

HRID 482634Notes

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.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>O1CCCC1>[CH3:16][S: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])(=[O:19])=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 195 milligrams (mg) (8.13 mM) of sodium hydride in 20 ml of anhydrous tetrahydrofuran was added, in portions, 2 g (8.13 mM) of the isopropyl 2-bromo-4-methyl-5-imidazolecarboxylate. The resulting suspension was cooled to 0° C. and 931 mg (8.13 mM) of methanesulfonyl chloride 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 2.4 g of desired product, isopropyl N-methylsulfonyl-2-bromo-4-methyl-5-imidazolecarboxylate as a yellow oil (93% yield).

Workup

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

Sources & evidence

ORD record: ord-f78a42c6a4ae4f83a8dd38cb266c77dd
Source dataset: uspto-grants-1986_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04574010

Reaction notes

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