Dimethylamine → HCID 4467695, compound

HRID 1446154Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]([C:13](O)=[O:14])=[C:11]([CH3:16])[O:10][N:9]=1.S(Cl)(Cl)=O.[CH3:21][NH:22][CH3:23]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]([C:13]([N:22]([CH3:23])[CH3:21])=[O:14])=[C:11]([CH3:16])[O:10][N:9]=1

Participants

Reactant 3

HCID 674Dimethylamine

HCID 24386Thionyl Chloride

HCID 902034-Isoxazolecarboxylic acid, 3-(2-chlorophenyl)-5-methyl-

Product 1

HCID 4467695HCID 4467695, compoundYield 23.6%

Conditions

Temperature: 60 °C

Procedure

To 3-(2-chlorophenyl)-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 (5 mg). HRMS (ESI, pos. ion) m/z calcd for C13H13ClN2O2: 264.0666, found 264.0669.

Workup

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

Sources & evidence

ORD record: ord-0d5037ad7476428a856729169b98b565
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666888B2

Reaction notes

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