Methanol → methyl (Z)-2-(2-dimethylaminomethylidenaminothiazol-4-yl)-2-methoxyiminoacetate

HRID 1377952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1377952
[Cl-].[CH3:2][N:3]([NH+]=CCl)[CH3:4].[NH2:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:18]/[O:19][CH3:20])/C(O)=O)[N:13]=1.[CH3:21][OH:22].[C:23](=[O:26])([O-])O.[Na+].O1CCC[CH2:29]1>>[CH3:2][N:3]([CH:4]=[N:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:18]\[O:19][CH3:20])/[C:21]([O:26][CH3:23])=[O:22])[N:13]=1)[CH3:29]

Komponenten

6

Edukt 5

HCID 887MethanolHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 5486924(alphaZ)-2-Amino-alpha-(methoxyimino)-4-thiazoleacetic acidHCID 86750850Dimethylaminochloromethyleneammonium chloride

Produkt 1

HCID 86750852methyl (Z)-2-(2-dimethylaminomethylidenaminothiazol-4-yl)-2-methoxyiminoacetateAusbeute 72 %

Versuchsvorschrift

Dimethylaminochloromethyleneammonium chloride (400 mg, 3.1 mmol) was dissolved in 10 ml of tetrahydrofuran. Added to the resulting solution were 300 mg of (Z)-2-(2-aminothiazol-4-yl)-2-methoxyimino-acetic acid, followed by stirring at room temperature for 16 hours. Methanol (10 ml) was added thereto. The mixture so obtained was stirred for 10 minutes at room temperature. The mixture was then poured into 50 ml of a saturated aqueous solution of sodium hydrogencarbonate. The mixture so obtained was extracted four times with 20 ml portions of chloroform. The extract was dried over anhydrous magnesium sulfate. The dried matter was then concentrated under reduced pressure. The residue was purified by chromatography on a silica gelcolumn, whereby 293 mg of the title compound were obtained (yield: 72%).

Aufarbeitung

  1. additionAdded to the resulting solution
  2. customThe mixture so obtained
  3. stirringwas stirred for 10 minutes at room temperature
  4. customThe mixture so obtained
  5. extractionwas extracted four times with 20 ml portions of chloroform
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. concentrationThe dried matter was then concentrated under reduced pressure
  8. customThe residue was purified by chromatography on a silica gelcolumn

Quellen und Nachweise

ORD-Eintrag
ord-824644153d46430aa334922fb4ffcaea
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05665888

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