Water → HCID 121386270, compound

HRID 2202870Notes

Reaction equation

HRID 2202870 reaction equation
[C:1]([O-:4])(O)=O.[Na+].[Br:6][C:7]1[CH:8]=[CH:9][C:10]2[N:14]=[C:13]([C:15](Cl)(Cl)Cl)[N:12]([CH3:19])[C:11]=2[CH:20]=1.C[C:22]#[N:23].[OH2:24]>>[Br:6][C:7]1[CH:8]=[CH:9][C:10]2[N:14]=[C:13]([C:15]([N:23]([O:4][CH3:1])[CH3:22])=[O:24])[N:12]([CH3:19])[C:11]=2[CH:20]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 516892Sodium Bicarbonate2×HCID 89690326HCID 89690326, compound

Product 1

HCID 121386270HCID 121386270, compound

Conditions

Temperature
60 °C

Procedure

NaHCO3 (717 mg) was added to a mixture of 6-bromo-1-methyl-2-(trichloromethyl)-1H-benzimidazole (400 mg), N,0-dimethylhydroxylamine hydrochloride (357 mg), NaHCO3 (512 mg), CH3CN (6 ml) and water (2 ml) at room temperature. The mixture was stirred at 60° C. overnight. The mixture was quenched with brine and extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (134 mg) as an orange gum.

Workup

  1. customThe mixture was quenched with brine
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-f5562eb55e4d48bab11ddb4ad6e3b164
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

Loading…