N-bromobutanimide → HCID 178432447, compound

HRID 1874852Notes

Reaction equation

HRID 1874852 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[NH:11][CH:12]=[C:13]([CH:15]=[O:16])[N:14]=1>CC#N>[Br:1][C:12]1[N:11]=[C:10]([CH3:9])[NH:14][C:13]=1[CH:15]=[O:16]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178418999HCID 178418999, compound

Product 1

HCID 178432447HCID 178432447, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-bromosuccinimide (0.900 g, 5.0 mmol) was added to a stirred solution of 2-methyl-1H-imidazole-4-carbaldehyde (0.500 g, 5.0 mmol) in CH3CN (50 mL). The reaction mixture was stirred for 3 days in the dark and then concentrated in the presence of silica gel. The absorbed crude material was purified by column chromatography (5-70% EtOAc/hexanes) to afford the title compound (0.334 g, 35%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 13.34 (br. s., 1H), 9.48 (s, 1H), 2.31 (s, 3H). ES-LCMS: m/z 189.2, 191.2 (M+1).

Workup

  1. concentrationthen concentrated in the presence of silica gel
  2. customThe absorbed crude material
  3. customwas purified by column chromatography (5-70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-809be7e2e1ff42788a8f94e4aef164b5
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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