Chlorosuccinimide → N-Hydroxy-2-(trifluoromethoxy)benzimidoyl chloride

HRID 1748150Notes

Reaction equation

HRID 1748150 reaction equation
C1C(=O)N([Cl:8])C(=O)C1.[F:9][C:10]([F:22])([F:21])[O:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1/[CH:14]=[N:15]/[OH:16]>CN(C)C=O.O>[F:9][C:10]([F:21])([F:22])[O:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1/[C:14](=[N:15]/[OH:16])/[Cl:8]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 58138479Benzaldehyde, 2-(trifluoromethoxy)-, oxime

Product 1

HCID 58138614N-Hydroxy-2-(trifluoromethoxy)benzimidoyl chloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

NCS (22 g, 166.04 mmol, 1.12 equiv) was slowly added to a stirred solution of (E)-2-(trifluoromethoxy)benzaldehyde oxime (30 g, 146.27 mmol, 1.00 equiv) in N,N-dimethylformamide (300 mL) keeping the internal temperature below 25°C. The reaction mixture was stirred fo(1 h at room temperature. The resulting solution was diluted with water (300 mL) and extracted with ethyl acetate (2×500 mL). The organic layers were combined, washed with brine (5×300 mL), dried over anhydrous sodium sulfate, and concentrated under vacuum to give (Z)-2-(trifluoromethoxy)benzoyl chloride oxime as a light yellow crystalline solid.

Workup

  1. customthe internal temperature below 25°C
  2. custom1 h
  3. customat room temperature
  4. extractionextracted with ethyl acetate (2×500 mL)
  5. washwashed with brine (5×300 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-998aa662b8394659914b96e9c821ccf1
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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