N-chlorosuccinamide → N-hydroxy-3-phenyl-4-(trifluoromethyl)isoxazole-5-carbimidoyl chloride

HRID 1506302Notes

Reaction equation

HRID 1506302 reaction equation
[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([CH:16]=[N:17][OH:18])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:19]NC(=O)CCC(N)=O>CN(C)C=O>[OH:18][N:17]=[C:16]([Cl:19])[C:10]1[O:9][N:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:11]=1[C:12]([F:13])([F:14])[F:15]

Participants

4

Reactant 2

HCID 15238416N-chlorosuccinamide2×HCID 136350288HCID 136350288, compound

Product 1

HCID 136350289N-hydroxy-3-phenyl-4-(trifluoromethyl)isoxazole-5-carbimidoyl chlorideYield 64.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-phenyl-4-(trifluoromethyl)isoxazole-5-carbaldehyde oxime (Intermediate I-12C, 0.34 g, 1.327 mmol) in N,N-dimethylformamide (1 mL) was added N-chlorosuccinamide (0.177 g, 1.327 mmol) in batches over a period of 2 min. at room temperature. The reaction mixture was stirred at room temperature for 30 min. An additional 0.09 g of N-chlorosuccinamide was added in one lot at room temperature and the contents were stirred for 20 min. The reaction mixture was partitioned between ethyl acetate (20 mL) and brine (2×20 mL). The ethyl acetate layer was dried over sodium sulfate and purified by silica gel column chromatography using hexane/ethyl acetate to yield N-hydroxy-3-phenyl-4-(trifluoromethyl)isoxazole-5-carbimidoyl chloride (0.250 g, 0.860 mmol, 64.8% yield) as a white solid. LC/MS M+1=291.2.

Workup

  1. stirringthe contents were stirred for 20 min
  2. customThe reaction mixture was partitioned between ethyl acetate (20 mL) and brine (2×20 mL)
  3. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-22691e81660b4652ae5b96309cbdb70f
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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