p-Toluenesulfonic acid → tert-butyl 2-[(E)-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylphenyl]methylideneamino]oxyacetate

HRID 1022839Notes

Reaction equation

HRID 1022839 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:23]([F:26])([F:25])[F:24])[O:13][N:12]=[C:11]([C:14]3[CH:21]=[CH:20][C:17]([CH:18]=O)=[C:16]([CH3:22])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:27]([O:31][C:32](=[O:36])[CH2:33][O:34][NH2:35])([CH3:30])([CH3:29])[CH3:28].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:27]([O:31][C:32](=[O:36])[CH2:33][O:34]/[N:35]=[CH:18]/[C:17]1[CH:20]=[CH:21][C:14]([C:11]2[CH2:10][C:9]([C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=3)([C:23]([F:26])([F:24])[F:25])[O:13][N:12]=2)=[CH:15][C:16]=1[CH3:22])([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 12919121tert-Butyl (aminooxy)acetateHCID 866585204-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehyde2×

Product 1

HCID 87403035tert-butyl 2-[(E)-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylphenyl]methylideneamino]oxyacetateYield 56%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzaldehyde (i.e. the product of Step 1, Example 1, 1.00 g), amino-oxyacetic-acid-tert-butyl-ester (403 mg), p-toluene sulfonic acid (43 mg) and toluene (20 mL) were heated to reflux for 30 min. After cooling, the mixture was washed with water, and the organic layer was dried over Na2SO4. After evaporation the residue was purified by flash chromatography on silica gel to yield the title compound (745 mg, 56%)

Workup

  1. temperaturewere heated
  2. temperatureto reflux for 30 min
  3. temperatureAfter cooling
  4. washthe mixture was washed with water
  5. dry with materialthe organic layer was dried over Na2SO4
  6. customAfter evaporation the residue
  7. customwas purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-4080817f084d4468b3caecc65252dbca
Source dataset
uspto-grants-2014_05
Patent number
US08722673B2

Reaction notes

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