Chlorosuccinimide → HCID 178499148, compound

HRID 1874848Notes

Reaction equation

HRID 1874848 reaction equation
[Cl: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>[Cl: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 31398ChlorosuccinimideHCID 178418785HCID 178418785, compound

Product 1

HCID 178499148HCID 178499148, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-chlorosuccinimide (0.318 g, 2.4 mmol) was added to a stirred solution of methyl 1H-imidazole-4-carboxylate (0.300 g, 2.4 mmol) in CH3CN (16 mL). The reaction mixture was stirred for 12 h in the dark and then concentrated. The white residue was taken up in EtOAc, satd. aqueous Na2S (10 mL) was added and the solution was stirred for 15 min. The organic layer was isolated, dried (Na2SO4), concentrated and the crude product was purified by column chromatography (20-70% EtOAc/hexanes) to afford the title compound (0.061 g, 16%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.05 (br. s., 1H), 7.85 (s, 1H), 3.81 (s, 3H). ES-LCMS: m/z 160.9, 162.9 (M+1).

Workup

  1. concentrationthen concentrated
  2. additionaqueous Na2S (10 mL) was added
  3. stirringthe solution was stirred for 15 min
  4. customThe organic layer was isolated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customthe crude product was purified by column chromatography (20-70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c888d540238342c6ae229826e62701f6
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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