Iodine chloride → N-(6-Iodo-2H-1,3-benzodioxol-5-yl)acetamide

HRID 577614

Reaktionsgleichung

Reaktionsgleichung von HRID 577614
[I:1]Cl.[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([NH:12][C:13](=[O:15])[CH3:14])=[CH:11][C:6]=2[O:5][CH2:4]1>C(Cl)Cl.C(O)(=O)C>[I:1][C:9]1[C:10]([NH:12][C:13](=[O:15])[CH3:14])=[CH:11][C:6]2[O:5][CH2:4][O:3][C:7]=2[CH:8]=1

Komponenten

5

Edukt 2

HCID 24640Iodine chlorideHCID 98688N-(2H-1,3-Benzodioxol-5-yl)acetamide

Produkt 1

HCID 53488067N-(6-Iodo-2H-1,3-benzodioxol-5-yl)acetamideAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A 1.0 M solution of iodine monochloride in methylene chloride (72.6 mL) was added dropwise to a solution of N-(benzo[d][1,3]dioxol-5-yl)acetamide (10 g, 55.8 mmol) in methylene chloride (66 mL) and acetic acid (11 mL). The mixture was stirred under nitrogen overnight and then washed with saturated sodium thiosulfate (2×150 mL) and brine (150 mL). The methylene chloride solution was dried (MgSO4) and evaporated, and the residue was purified by column chromatography on silica gel (CH2Cl2/petroleum at 20/1) to obtain N-(6-iodobenzo[d][1,3]dioxol-5-yl)acetamide (3.7 g, 22%) as a white solid. LCMS: 306 [M+1]+; 1H NMR (DMSO-d6) δ 2.00 (s, 3H), 6.06 (s, 2H), 6.95 (s, 1H), 7.37 (s, 1H), 9.34 (s, 1H).

Aufarbeitung

  1. washwashed with saturated sodium thiosulfate (2×150 mL) and brine (150 mL)
  2. dry with materialThe methylene chloride solution was dried (MgSO4)
  3. customevaporated
  4. customthe residue was purified by column chromatography on silica gel (CH2Cl2/petroleum at 20/1)

Quellen und Nachweise

ORD-Eintrag
ord-e4b007956c8947f797e3bc82960372b8
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040556B2

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