N-bromobutanimide → HCID 178499145, compound

HRID 1874850Notes

Reaction equation

HRID 1874850 reaction equation
[Br:1]N1C(=O)CCC1=O.[NH:9]1[CH:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[N:11]=[CH:10]1>CC#N>[Br:1][C:13]1[N:9]=[CH:10][NH:11][C:12]=1[C:14]([O:16][CH3:17])=[O:15]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178418785HCID 178418785, compound

Product 1

HCID 178499145HCID 178499145, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-bromosuccinimide (0.900 g, 5.0 mmol) was added to a stirred solution of methyl 1H-imidazole-4-carboxylate (0.630 g, 5.0 mmol) in CH3CN (50 mL). The reaction mixture was stirred for 12 h in the dark and then concentrated in the presence of silica gel. The absorbed crude material was purified by column chromatography (20-100% EtOAc/hexanes) to afford the title compound (0.708 g, 70%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.00 (br. s., 1H), 7.81 (s, 1H), 3.81 (s, 3H). ES-LCMS: m/z 204.9, 206.9 (M+1).

Workup

  1. concentrationthen concentrated in the presence of silica gel
  2. customThe absorbed crude material
  3. customwas purified by column chromatography (20-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f494e0b71471421f86d88f51d16b3f7c
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

Loading…