Methyl chloroformate → Methyl 3-cyano-4-(isopropylsulfonyl)phenylcarbamate

HRID 1667611Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1667611
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])=[C:6]([CH:9]=1)[C:7]#[N:8].Cl[C:17]([O:19][CH3:20])=[O:18]>N1C=CC=CC=1>[C:7]([C:6]1[CH:9]=[C:2]([NH:1][C:17](=[O:18])[O:19][CH3:20])[CH:3]=[CH:4][C:5]=1[S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])#[N:8]

Komponenten

4

Edukt 2

HCID 6586Methyl chloroformateHCID 574482075-Amino-2-(isopropylsulfonyl)benzonitrile

Produkt 1

HCID 57448208Methyl 3-cyano-4-(isopropylsulfonyl)phenylcarbamateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To 15C (450 mg, 2 mmol) in pyridine (10 mL) at 0° C. was added methyl chloroformate (0.8 mL, 10 mmol). The reaction was stirred at 0° C. for 20 min, then warmed to rt for 2 h. The reaction was concentrated, then diluted with ethyl acetate, washed with brine, dried (Na2SO4), filtered and concentrated. The resulting residue was purified via silica gel chromatography (0-60% ethyl acetate/hexanes) to provide 15D (490 mg, 88%). LC-MS: 283.35 (M+H)+.

Aufarbeitung

  1. temperaturewarmed to rt for 2 h
  2. concentrationThe reaction was concentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified via silica gel chromatography (0-60% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8b6db5b81d474600a0ed62124ad27042
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044242B2

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