Triacetoxyperiodinane → HCID 57786062, compound

HRID 1399155Notes

Reaction equation

HRID 1399155 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]3=[N:14][C:15]4[C:20]([Cl:21])=[CH:19][CH:18]=[C:17]([CH2:22][OH:23])[C:16]=4[N:12]3[CH2:11][CH2:10][CH2:9]2)=[C:4]([Cl:24])[CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]3=[N:14][C:15]4[C:16](=[C:17]([CH:22]=[O:23])[CH:18]=[CH:19][C:20]=4[Cl:21])[N:12]3[CH2:11][CH2:10][CH2:9]2)=[C:4]([Cl:24])[CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57785919HCID 57785919, compound

Product 1

HCID 57786062HCID 57786062, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of [1-(4-bromo-2-chlorophenyl)-9-chloro-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methanol (1.24 g, 2.924 mmol) in dimethylsulfoxide (25.0 mL) was added Dess-Martin reagent (1.36 g, 3.216 mmol). The reaction mixture was stirred at room temperature for 2 hrs. The mixture was quenched with aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium thiosulfate and extracted with ethyl acetate (×3). The combined organic layer was washed with water (×2) and brine (×1), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The resulting solid was washed with ethyl acetate/diisopropyl ether to give the title compound as a pale yellow solid (1.20 g, 2.82 mmol, 97%).

Workup

  1. customThe mixture was quenched with aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium thiosulfate
  2. extractionextracted with ethyl acetate (×3)
  3. washThe combined organic layer was washed with water (×2) and brine (×1)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washThe resulting solid was washed with ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-a6bb1959dc8f4a5ab9b62066b37778df
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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