Water → HCID 178526351, compound

HRID 2096975Notes

Reaction equation

HRID 2096975 reaction equation
Cl[N:2]1[C:6](=O)[CH2:5][CH2:4]C1=O.[F:9][C:10]1[C:18]([I:19])=[CH:17][CH:16]=[CH:15][C:11]=1[CH:12]=[N:13][OH:14].O.C1(N)CC1>CN(C=O)C>[CH:6]1([NH:2][C:12](=[N:13][OH:14])[C:11]2[CH:15]=[CH:16][CH:17]=[C:18]([I:19])[C:10]=2[F:9])[CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 962Water2×HCID 31398ChlorosuccinimideHCID 69828CyclopropylamineHCID 76688560HCID 76688560, compound

Product 1

HCID 178526351HCID 178526351, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

N-chlorosuccinimide (1.20 g, 8.9 mmol) was added portionwise to a stirred solution of 2-fluoro-3-iodobenzaldehyde oxime (preparation 22e, 2.15 g, 8.1 mmol) in N,N′-dimethylformamide (3 mL) and the mixture was stirred for 15 minutes at 55° C. After cooling to ambient temperature, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and evaporated. The residue was taken up in tetrahydrofuran (10 mL), cooled by means of an ice-water bath and cyclopropylamine (2.90 mL, 41.9 mmol) was added dropwise. After stirring 3 hours at room temperature, water was added to the reaction and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and evaporated to give the title compound (2.53 g, 96%) as a white solid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. temperaturecooled by means of an ice-water bath
  7. stirringAfter stirring 3 hours at room temperature
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe organic layer was washed with brine
  10. dry with materialdried (MgSO4)
  11. customevaporated

Sources & evidence

ORD record
ord-78b6740596bb4929a6b89fc1f84dc98c
Source dataset
uspto-grants-2013_05
Patent number
US08450341B2

Reaction notes

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