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

HRID 1360912Notes

Reaction equation

HRID 1360912 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 desiccant 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. filtrationdesiccant 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-620baf2608d34dcebfdff9a4d3a7b287
Source dataset
uspto-grants-2011_02
Patent number
US07879895B2

Reaction notes

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