Triethylamine → (+/-)-5-(2,6-Dichlorophenyl)-3-(3-nitrophenyl)-2-isoxazoline

HRID 2053387Notes

Reaction equation

HRID 2053387 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10](Cl)=[N:11][OH:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Cl:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:16]=1[CH:17]=[CH2:18].C(N(CC)CC)C>C1COCC1>[Cl:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:16]=1[CH:17]1[O:12][N:11]=[C:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:18]1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 342542,6-DichlorostyreneHCID 2756318alpha-Chloro-3-nitrobenzaldoxime

Product 1

HCID 69221841(+/-)-5-(2,6-Dichlorophenyl)-3-(3-nitrophenyl)-2-isoxazoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Nitro-N-hydroxybenzenecarboximidoyl chloride (1.16 g, 5.78 mmol) and 2,6-dichlorostyrene (1.0 g, 5.78 mmol) were dissolved in anhydrous THF (20 mL) and triethylamine (1.21 mL, 8.67 mmol). Upon addition of triethylamine a while solid formed. After 3 h this solid was collected by filtration under reduced pressure to provide the title compound as a white solid.

Workup

  1. customformed
  2. filtrationAfter 3 h this solid was collected by filtration under reduced pressure

Sources & evidence

ORD record
ord-73f9f14d9f514b97b18ad1a80624141f
Source dataset
uspto-grants-2008_02
Patent number
US07326790B2

Reaction notes

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