N-bromobutanimide → HCID 67364381, compound
Reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([O:13][C:14]([N:16]1[CH2:25][C:24]2[N:20]([CH:21]=[N:22][N:23]=2)[C:19]2[CH:26]=[CH:27][C:28]([Cl:30])=[CH:29][C:18]=2[CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>O1CCCC1>[C:9]([O:13][C:14]([N:16]1[CH2:25][C:24]2[N:20]([C:21]([Br:1])=[N:22][N:23]=2)[C:19]2[CH:26]=[CH:27][C:28]([Cl:30])=[CH:29][C:18]=2[CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]Participants
4
Procedure
N-Bromosuccinimide (4.50 g, 24.0 mmol) was added to 8-chloro-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulene-5-carboxylic acid tert-butyl ester (7.00 g, 21.8 mmol) in tetrahydrofuran (140 ml). The mixture was stirred in boiling tetrahydrofuran for 2 hours. The solvent was removed in vacuo and the residue was purified by chromatography (50 g silica gel, heptane: ethylacetate 1:9 to 1:0) to yield 7.39 g (85%) 1-bromo-8-chloro-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulene-5-carboxylic acid tert-butyl ester as white solid. MS m/e: 401 (M+H+).