Acetone → 1-Chloro-2-(5,6-dichloro-1-methyl-1H-benzoimidazol-2-yl)-propan-2-ol

HRID 1394466Notes

Reaction equation

HRID 1394466 reaction equation
[Cl:1][C:2]1[C:14]([Cl:15])=[CH:13][C:5]2[N:6]([CH3:12])[C:7](C(C)=C)=[N:8][C:4]=2[CH:3]=1.[Cl:16]N1C(=O)N(Cl)C(=O)N(Cl)C1=O.[CH3:28][C:29]([CH3:31])=[O:30]>O>[Cl:16][CH2:28][C:29]([C:7]1[N:6]([CH3:12])[C:5]2[CH:13]=[C:14]([Cl:15])[C:2]([Cl:1])=[CH:3][C:4]=2[N:8]=1)([OH:30])[CH3:31]

Participants

5

Reactant 3

HCID 180AcetoneHCID 6909Trichloroisocyanuric AcidHCID 669690955,6-dichloro-1-methyl-2-isopropenyl-1H-benzimidazole

Product 1

HCID 116522571-Chloro-2-(5,6-dichloro-1-methyl-1H-benzoimidazol-2-yl)-propan-2-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5,6-dichloro-1-methyl-2-isopropenyl-1H-benzimidazole (2.5 g) in acetone (30 mL) and water (6 mL) at room temperature was added trichloroisocyanuric acid (845 mg). The resulting mixture was stirred at room temperature for 18 h. The reaction mixture was quenched with water, extracted with EtOAc, and dried over Na2SO4. After removal of the dessicant by filtration, concentration yielded an orange crude oil. The crude product was purified by flash chromatography (10%-40% EtOAc/hexanes) to yield the title compound as a yellow solid.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. customAfter removal of the
  5. filtrationdessicant by filtration, concentration
  6. customyielded an orange crude oil
  7. customThe crude product was purified by flash chromatography (10%-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f23e3eaf0e534f78a91fddf5effe4217
Source dataset
uspto-grants-2008_03
Patent number
US07348438B2

Reaction notes

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