Dimethylformamide → methyl (E)-2-(2-dimethylaminomethylidenaminothiazol-4-yl)-2-methoxyiminoacetate

HRID 266248

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:11]/[O:12][CH3:13])/[C:8]([OH:10])=[O:9])[N:6]=1.[CH3:14][N:15]([CH3:18])[CH:16]=O.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].O1CCC[CH2:27]1>CO>[CH3:14][N:15]([CH:18]=[N:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:11]/[O:12][CH3:13])/[C:8]([O:10][CH3:27])=[O:9])[N:6]=1)[CH3:16]

Participants

Conditions

Temperature: 5 °C

Procedure

(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid (0.5 g, 2.5 mmol) was dissolved in 20 ml of tetrahydrofuran. Subsequent to the addition of 0.72 g (9.9 mmol) of dimethylformamide, the resulting solution was cooled to 5° C. The solution was added with 1.52 g (9.9 mmol) of phosphorus oxychloride and the resulting mixture was stirred for 3 hours. Methanol (20 ml) was added to the reaction mixture, followed by stirring for 10 minutes. A 2N aqueous solution of sodium hydroxide was added to the reaction mixture to adjust its pH to 7. The reaction mixture so obtained was extracted three times with 100 ml portions of chloroform. The organic phases were combined and then dried. The solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column, whereby 0.63 g of the title compound was obtained (yield: 94%).

Workup

stirringby stirring for 10 minutes
customThe reaction mixture so obtained
extractionwas extracted three times with 100 ml portions of chloroform
customdried
distillationThe solvent was distilled off under reduced pressure
customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record: ord-0da2f22b3d394e28aac059438636dbe2
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05650518

Linked notes

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