Chlorosuccinimide → HCID 178454347, compound

HRID 1875063Notes

Reaction equation

[Cl:1]N1C(=O)CCC1=O.[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]>C(#N)C>[CH3:12][C:10]([O:13][C:14]([N:16]([C:24]1[NH:28][C:27]([CH:29]=[O:30])=[C:26]([Cl:1])[N:25]=1)[C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])=[O:15])([CH3:9])[CH3:11]

Participants

Conditions

Temperature: 60 °C

Procedure

N-Chlorosuccinimide (0.346 g, 2.59 mmol) was added to a suspension of bis(1,1-dimethylethyl)(4-formyl-1H-imidazol-2-yl)imidodicarbonate (0.672 g, 2.158 mmol) in acetonitrile (10 mL). The mixture was heated at 60° C. for 2 hrs. The solvent was evaporated. Chromatography of the residue with ethyl acetate:hexane gave the title compound (0.086 g, 11%) as a white solid. 1H NMR (400 MHz, chloroform-d) δ ppm 10.38-10.79 (m, 1H), 9.6 (s, 1H), 1.52 (s, 18H). ES MS: m/z 345

Workup

customThe solvent was evaporated

Sources & evidence

ORD record: ord-629ea1e83bdc44b1b8ab43a9d88aa9dd
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304419B2

Reaction notes

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