Phosphorus oxychloride → HCID 89690996, compound

HRID 2203048Notes

Reaction equation

HRID 2203048 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH:10]3[CH2:13][CH:12]([CH:14]=[N:15]O)[CH2:11]3)[N:7]([CH3:17])[C:6]=2[CH:18]=1.P(Cl)(Cl)(Cl)=O>CC#N>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH:10]3[CH2:13][CH:12]([C:14]#[N:15])[CH2:11]3)[N:7]([CH3:17])[C:6]=2[CH:18]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 89691114HCID 89691114, compound

Product 1

HCID 89690996HCID 89690996, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 1-(3-(6-bromo-1-methyl-1H-benzimidazol-2-yl)cyclobutyl)-N-hydroxymethanimine (100 mg) in CH3CN (10 ml) was added phosphorous oxychloride (1 ml), and the mixture was stirred at room temperature for 16 h. The mixture was then concentrated in vacuo and poured into saturated NaHCO3 solution. The mixture was extracted with DCM, and the organic layer was washed with brine, dried over Na2SO4 and purified by column chromatography (MeOH/DCM) to afford the title compound (50 mg) as a yellow solid.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. additionpoured into saturated NaHCO3 solution
  3. extractionThe mixture was extracted with DCM
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. custompurified by column chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-5edd8295fb6d418b847f49b6c68fb734
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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