Methyl chloroformate → Dimethyl(4-iodo-5-methylpyridin-2-yl)imidodicarbonate

HRID 537031Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 537031
[I:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([NH2:9])[CH:3]=1.CCN(C(C)C)C(C)C.[C:19](Cl)(=[O:22])[O:20][CH3:21]>C(Cl)Cl.[NH4+].[Cl-]>[CH3:21][O:20][C:19]([N:9]([C:4]1[CH:3]=[C:2]([I:1])[C:7]([CH3:8])=[CH:6][N:5]=1)[C:19]([O:20][CH3:21])=[O:22])=[O:22]

Komponenten

6

Edukt 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 667478634-Iodo-5-methylpyridin-2-amine

Produkt 1

HCID 66748316Dimethyl(4-iodo-5-methylpyridin-2-yl)imidodicarbonateAusbeute 82,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 4-iodo-5-methylpyridin-2-amine (90 g, 380 mmol) in DCM (3800 mL) were added DIEA (192 mL, 930 mmol) and methyl carbonochloridate (58.8 mL, 760 mmol) at 0° C. The reaction mixture was allowed to stir at 0° C. for 1 h and was then diluted with aqueous saturated NH4Cl. The organic solvent was separated and the aqueous solution was extracted with DCM. The organic solutions were combined, washed with brine and concentrated to give dimethyl(4-iodo-5-methylpyridin-2-yl)imidodicarbonate (110 g, 80%) which was used in the next step without purification.

Aufarbeitung

  1. customThe organic solvent was separated
  2. extractionthe aqueous solution was extracted with DCM
  3. washwashed with brine
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6959c635703c404d9483d1aa579afcd7
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859768B2

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