Dimethylamine → HCID 24809797, compound

HRID 1446153Notes

Reaction equation

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

Participants

Reactant 3

HCID 674Dimethylamine

HCID 24386Thionyl Chloride

HCID 14880933-(4-Chlorophenyl)-5-methyl-1,2-oxazole-4-carboxylic acid

Product 1

HCID 24809797HCID 24809797, compoundYield 23.6%

Conditions

Temperature: 60 °C

Procedure

To 3-(4-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, 2 M in THF) 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 264.0671.

Workup

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

Sources & evidence

ORD record: ord-0fd667abab7c4c9dab4639b08a3be5e4
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666888B2

Reaction notes

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