Chlorosuccinimide → Methyl 3-(2,6-dichlorophenyl)-5-(propan-2-yl)-1,2-oxazole-4-carboxylate

HRID 2251318Notes

Reaction equation

HRID 2251318 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[CH:4]=[N:5][OH:6].ClN1C(=O)[CH2:16][CH2:15][C:14]1=O.CC[C:22]([O:24][C:25]([CH:27]([CH3:29])C)=[O:26])=O.C[O-].[Na+].ClC1C=CC=C(Cl)C=1C(Cl)=NO>CN(C)C=O.O1CCCC1.O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]1[C:27]([C:25]([O:24][CH3:22])=[O:26])=[C:29]([CH:15]([CH3:16])[CH3:14])[O:6][N:5]=1

Participants

9

Reactant 5

HCID 31398ChlorosuccinimideHCID 91328Benzaldehyde, 2,6-dichloro-, oximeHCID 28001642,6-DichlorobenzaldchloroximeHCID 10942334Sodium MethoxideHCID 22025518HCID 22025518, compound

Product 1

HCID 22176607Methyl 3-(2,6-dichlorophenyl)-5-(propan-2-yl)-1,2-oxazole-4-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2,6-dichlorobenzaldehyde oxime (19.8 g, 0.104 mol) in N,N-dimethyl formamide (80 mL) was placed in an ambient temperature water bath and was treated with N-chlorosuccinimide (13.9 g, 0.104 mole). Following dissolution, an exotherm was observed along with a color change to dark yellow. The reaction was stirred an additional hour then the contents were then poured into water (200 mL) and the product extracted with diethyl ether (300 mL). The ethereal layer was washed with water (3×100 mL) and brine (50 mL), then dried over anhydrous magnesium sulfate. After filtering, the solvent was removed in vacuo to yield a yellow oil which was used in the next step without further purification. Separately, a solution of methyl isobutyryl acetate (18 g, 0.125 mol) in tetrahydrofuran (25 mL) at 0° C. was treated with a solution of sodium methoxide (250 mL, 0.5 M in methanol). A solution of the above crude 2,6-dichloro-N-hydroxybenzenecarboximidoyl chloride in tetrahydrofuran (80 mL) was then added dropwise. After stirring at ambient temperature for 16 h the solvent was removed in vacuo. The residue was triturated with water (250 mL) and the resulting solids filtered and washed with water. Yield=22.7 g. (69%) of methyl 3-(2,6-dichlorophenyl)-5-isopropylisoxazole-4-carboxylate.

Workup

  1. customwas placed in an ambient temperature
  2. dissolutiondissolution
  3. extractionthe product extracted with diethyl ether (300 mL)
  4. washThe ethereal layer was washed with water (3×100 mL) and brine (50 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtering
  7. customthe solvent was removed in vacuo
  8. customto yield a yellow oil which
  9. customwas used in the next step without further purification
  10. stirringAfter stirring at ambient temperature for 16 h the solvent
  11. customwas removed in vacuo
  12. customThe residue was triturated with water (250 mL)
  13. filtrationthe resulting solids filtered
  14. washwashed with water

Sources & evidence

ORD record
ord-0f24fb7cb4c6411cb70392c2e3b9fc7a
Source dataset
uspto-grants-2008_01
Patent number
US07319109B2

Reaction notes

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