Methylamine → 3-iodo-N-methylbenzamide

HRID 38224

Reaktionsgleichung

Reaktionsgleichung von HRID 38224
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[CH3:11][NH2:12].C1COCC1>C(Cl)Cl>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:12][CH3:11])=[O:6]

Komponenten

5

Edukt 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 743783-Iodobenzoyl chloride

Produkt 1

HCID 33843663-iodo-N-methylbenzamideAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a cooled (0° C.) solution of 3-iodobenzoyl chloride (2.66 g; 10.0 mmol) in DCM (10 mL) was slowly added a 2 M solution of methylamine in THF (10 mL, 2.0 eq.). Upon completion of the addition, the ice bath was removed and the mixture was stirred overnight. All volatiles were removed in vacuo and the residue was treated with aq. NaHCO3 (25 mL) and subsequently extracted with ethyl acetate (3×15 mL). The combined organic layers were dried over MgSO4 and evaporated. The crude product was purified by column chromatography on silica gel to give the desired 3-iodo-N-methylbenzamide (0.67 g, 26% yield).

Aufarbeitung

  1. additionUpon completion of the addition
  2. customthe ice bath was removed
  3. customAll volatiles were removed in vacuo
  4. additionthe residue was treated with aq. NaHCO3 (25 mL)
  5. extractionsubsequently extracted with ethyl acetate (3×15 mL)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. customevaporated
  8. customThe crude product was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-2ccd5342a78a44c68040cb5a8f689b09
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524724B2

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