Chloroform → 12-Chloro-9-fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513762Notes

Reaction equation

HRID 513762 reaction equation
CN1C(C)(C)C(=O)N(C)C1=O.[F:12][C:13]1[CH:30]=[C:29]2[C:16]([S:17](=[O:32])(=[O:31])[NH:18][C:19]3[C:28]2=[CH:27][CH:26]=[C:25]2[C:20]=3[N:21]=[CH:22][CH:23]=[CH:24]2)=[CH:15][CH:14]=1.C(Cl)(Cl)[Cl:34]>>[Cl:34][C:26]1[CH:27]=[C:28]2[C:19](=[C:20]3[C:25]=1[CH:24]=[CH:23][CH:22]=[N:21]3)[NH:18][S:17](=[O:31])(=[O:32])[C:16]1[C:29]2=[CH:30][C:13]([F:12])=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 6212ChloroformHCID 617941,3-Dimethyl-5,5-dimethylhydantoinHCID 167599219-fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

Product 1

HCID 6818318212-Chloro-9-fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 69%

Conditions

Temperature
70 °C

Procedure

1,3-dimethyl-5,5-dimethylhydantoin (0.73 g, 36.7 mmol) was added to a solution of 9-fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide 187 (1.0 g, 33.3 mmol) in chloroform (40 ml) and the reaction was heated at 70° C. until the starting material was consumed (LCMS). After cooling, the mixture was concentrated in vacuo. The residue was dissolved in EtOAc and the organic phase was washed with sodium metabisulfate, water and brine. The organic phase was dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with DCM/MeOH (99:1) as the eluent to give the title compound (0.8 g, 69%).

Workup

  1. customwas consumed (LCMS)
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washthe organic phase was washed with sodium metabisulfate, water and brine
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by column chromatography with DCM/MeOH (99:1) as the eluent

Sources & evidence

ORD record
ord-8bc46504056948c28e1870549b252ddf
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…