N-bromobutanimide → HCID 178454341, compound

HRID 1875071Notes

Reaction equation

HRID 1875071 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][C:10]([O:13][C:14]([N:16]([C:24]1[NH:25][CH:26]=[C:27]([CH:29]=[O:30])[N:28]=1)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:15])([CH3:12])[CH3:11]>CN(C=O)C.CCOC(C)=O>[CH3:12][C:10]([O:13][C:14]([N:16]([C:24]1[NH:28][C:27]([CH:29]=[O:30])=[C:26]([Br:8])[N:25]=1)[C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])=[O:15])([CH3:9])[CH3:11]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 178454349HCID 178454349, compound

Product 1

HCID 178454341HCID 178454341, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

NBS (0.206 g, 1.156 mmol) was added to a solution of bis(1,1-dimethylethyl)(4-formyl-1H-imidazol-2-yl)imidodicarbonate (0.300 g, 0.964 mmol) in DMF (3 mL). The mixture was heated at 50° C. for 3 hrs. The reaction mixture was diluted with EtOAc and washed 2× with water. The organic layer was dried over sodium sulfate and concentrated. Chromatography (EtOAc:hexane) gave the desired product (0.154 g, 41%) as a white solid. 1H NMR (400 MHz, chloroform-d) δ ppm 10.54 (br. s., 1H), 9.54 (s, 1H), 1.50 (s, 18H). ES MS: m/z 390.

Workup

  1. washwashed 2× with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-956a36d279c84215adbfb5cd41db232e
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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