Chlorosuccinimide → (Z)-N-hydroxy-4-(trifluoromethoxy)benzimidoyl chloride

HRID 1475260

Reaction equation

HRID 1475260 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:12]=[CH:11][C:7]([CH:8]=[N:9][OH:10])=[CH:6][CH:5]=1.[Cl:15]N1C(=O)CCC1=O>CN(C=O)C>[OH:10]/[N:9]=[C:8](\[Cl:15])/[C:7]1[CH:11]=[CH:12][C:4]([O:3][C:2]([F:13])([F:14])[F:1])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 2777199p-Trifluoromethoxybenzaldehyde oxime

Product 1

HCID 12096320(Z)-N-hydroxy-4-(trifluoromethoxy)benzimidoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(trifluoromethoxy)benzaldehyde oxime (9.5 g, 46 mmol) in DMF (80 ml) was added N-chlorosuccinimide (8.0 g, 60 mmol) and the resulting mixture was stirred at RT for 5 h. The volatiles were removed under reduced pressure and the residue was dissolved in EtOAc, and washed with H2O, brine. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The solid residue was used without further purification for the following step. 1H NMR (500 MHz, CDCl3) δ 7.78 (d, J=7.2 Hz, 2H), 7.13 (d, J=6.8 Hz, 2H).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with H2O, brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe solid residue was used without further purification for the following step

Sources & evidence

ORD record
ord-99c499aaafe343a1b83f74cf70c68bc8
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Linked notes

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