Dimethylamine → 3-(2,6-Dichlorophenyl)-N,N,5-trimethylisoxazole-4-carboxamide

HRID 1446155Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([C:14](O)=[O:15])=[C:12]([CH3:17])[O:11][N:10]=1.S(Cl)(Cl)=O.[CH3:22][NH:23][CH3:24]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([C:14]([N:23]([CH3:24])[CH3:22])=[O:15])=[C:12]([CH3:17])[O:11][N:10]=1

Participants

Reactant 3

HCID 674Dimethylamine

HCID 24386Thionyl Chloride

HCID 775214-Isoxazolecarboxylic acid, 3-(2,6-dichlorophenyl)-5-methyl-

Product 1

HCID 28042603-(2,6-Dichlorophenyl)-N,N,5-trimethylisoxazole-4-carboxamideYield 41.8%

Conditions

Temperature: 60 °C

Procedure

To 3-(2,6-dichlorophenyl)-5-methylisoxazol-4-carboxylic acid (25 mg, 0.10 mmol) was added thionyl chloride (1 mL) and the neat solution allowed to stir 60° C. After 30 min, excess thionyl chloride was evaporated and dimethyl amine (40 μL, 0.08 mmol, 2M in tetrahydrofuran) was added and allowed to stir overnight at ambient temperature. The residue was purified using reversed phase HPLC to afford the title compound (10 mg). HRMS (ESI, pos. ion) m/z calcd for C13H12Cl2N2O2: 298.0276, found 298.0276.

Workup

customexcess thionyl chloride was evaporated
stirringto stir overnight at ambient temperature
customThe residue was purified

Sources & evidence

ORD record: ord-197441134b124f52a031015688d32cb7
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666888B2

Reaction notes

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