Iodine → tert-Butyl 4-amino-3-iodobenzylcarbamate

HRID 966532Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 966532
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Ca+2].[I:22]I>CO>[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:15])=[C:13]([I:22])[CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 807IodineHCID 10112Calcium CarbonateHCID 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamate

Produkt 1

HCID 10383091tert-Butyl 4-amino-3-iodobenzylcarbamateAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a mixture of (4-amino-benzyl)-carbamic acid tert-butyl ester (4.8 g, 21.6 mmol) and calcium carbonate (2.7 g, 27 mmol) in methanol (60 mL) was added iodine (5.5 g, 21.6 mmol) in portions. The mixture was heated at reflux overnight and then concentrated in vacuo to give a dark brown residue, which was partitioned between ethyl acetate and saturated sodium bisulfite solution. The organic phase was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give a residue, which was purified by chromatography (5%-20% ethyl acetate in hexanes) to give 3.5 g (47%) of the desired product as a brown semi-solid. MS(APCI+): m/z 349.1 (MH+).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated in vacuo
  4. customto give a dark brown residue, which
  5. customwas partitioned between ethyl acetate and saturated sodium bisulfite solution
  6. washThe organic phase was washed with water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo
  10. customto give a residue, which
  11. customwas purified by chromatography (5%-20% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-0e25684666ea4fcb97dd193a43e2935f
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06951848B2

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