N-bromobutanimide → HCID 178499145, compound
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
Product 1
Reagents, catalysts & solvents 1
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
- concentrationthen concentrated in the presence of silica gel
- customThe absorbed crude material
- 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
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