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

HRID 1360968Notes

Reaction equation

HRID 1360968 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-daf59fee5fa34919b3c1a7a45ab7d0c3
Source dataset
uspto-grants-2011_02
Patent number
US07879895B2

Reaction notes

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