Methylamine → 5-bromo-N,2-dimethylbenzamide

HRID 77387

Reaktionsgleichung

Reaktionsgleichung von HRID 77387
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].[CH:12]([N:15](CC)C(C)C)(C)C.CN.O1CCCC1.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.C(OCC)(=O)C>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([NH:15][CH3:12])=[O:8]

Komponenten

8

Edukt 6

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 3460045-Bromo-2-methylbenzoic acid

Produkt 1

HCID 231569135-bromo-N,2-dimethylbenzamideAusbeute 94,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
2 °C

Versuchsvorschrift

To a solution of 5-bromo-2-methylbenzoic acid (2.325 mmol, 0.5 g) in dichloromethane (25 mL) under nitrogen was added N,N-diisopropylethylamine (0.75 g, 5.8 mmol). Reaction then cooled in an ice bath to 2° C. and the yellow solution treated with 2M methylamine in tetrahydrofuran (3.49 mL, 6.98 mmol) over 5 minutes, followed by 1-propanephosphonic acid cyclic anhydride as a 50% wt solution in ethyl acetate (2.08 mL, 3.49 mmol) added dropwise. The ice bath was then removed and stirring continued overnight. The mixture was purified on silica (15 g column on Isolera 4) eluting with 0-5% methanol in dichloromethane to afford 5-Bromo-N,2-dimethylbenzamide (0.5 g, 2.2 mmol).

Aufarbeitung

  1. customReaction
  2. additionadded dropwise
  3. customThe ice bath was then removed
  4. customThe mixture was purified on silica (15 g column on Isolera 4)
  5. washeluting with 0-5% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-615c3d162ed9479c98fc676cd4fdb006
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841289B2

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