Water → 1-(5,6-Dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone oxime

HRID 2043301Notes

Reaction equation

HRID 2043301 reaction equation
[Cl:1][C:2]1[C:16]([Cl:17])=[CH:15][C:5]2[NH:6][C:7]([C:9](=O)[C:10]([F:13])([F:12])[F:11])=[N:8][C:4]=2[CH:3]=1.Cl.[NH2:19][OH:20].O>N1C=CC=CC=1.C(O)C>[Cl:1][C:2]1[C:16]([Cl:17])=[CH:15][C:5]2[NH:6][C:7]([C:9](=[N:19][OH:20])[C:10]([F:13])([F:12])[F:11])=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 962Water2×HCID 443297Hydroxyamine hydrochlorideHCID 115943701-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone

Product 1

HCID 1363601451-(5,6-Dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

1-(5,6-Dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone (0.3005 g; 1.062 mmoles) and hydroxylamine hydrochloride (0.2389 g, 3.438 mmoles) were suspended in pyridine (3 mL) and ethanol (3 mL), then heated to 70° C. for 3 hrs. The reaction mixture was cooled to room temperature, water was water (50 mL) and the reaction mixture was then extracted with ethyl acetate (3×40 ml). The extracts were combined then washed with water (20 mL), brine (30 mL) and dried over Na2SO4. The filtrate was concentrated in vacuo and purified by column chromatography (SiO2; 30% ethyl acetate/CH2Cl2) to yield the title compound as an off-white solid, as a mixture of oxime E and Z isomers.

Workup

  1. extractionthe reaction mixture was then extracted with ethyl acetate (3×40 ml)
  2. washThe extracts were combined then washed with water (20 mL), brine (30 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified by column chromatography (SiO2; 30% ethyl acetate/CH2Cl2)

Sources & evidence

ORD record
ord-19cbfcb23c744f46aff8548b738b220f
Source dataset
uspto-grants-2013_11
Patent number
US08586616B2

Reaction notes

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