2,6-Lutidine → N-(cyanomethyl)-2-hydroxy-4-methoxy-N-methylbenzamide

HRID 639931

Reaktionsgleichung

Reaktionsgleichung von HRID 639931
[OH:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:13][NH:14][CH2:15][C:16]#[N:17].N1C(C)=CC=CC=1C>C(Cl)Cl>[C:16]([CH2:15][N:14]([CH3:13])[C:4](=[O:5])[C:3]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:2]=1[OH:1])#[N:17]

Komponenten

5

Edukt 3

HCID 79372,6-LutidineHCID 36652Acetonitrile, 2-(methylamino)-HCID 231185592-Hydroxy-4-methoxybenzoyl chloride

Produkt 1

HCID 55207279N-(cyanomethyl)-2-hydroxy-4-methoxy-N-methylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-hydroxy-4-methoxybenzoyl chloride (22.19 g, 118.9 mmol) in 500 CH2Cl2 were added (methylamino)acetonitrile (10 g, 142.7 mmol) and 2,6-lutidine (19.1 g, 178.4 mmol). The reaction was stirred at rt overnight. The reaction mixture was then partitioned between EtOAc and 1(N) aq HCl. Organic layer washed with 1(N) aq HCl (2×), dried over Na2SO4 and concentrated to light yellow viscous material (24.63 g, 94%). This material was used in the next step without further purification.

Aufarbeitung

  1. customThe reaction mixture was then partitioned between EtOAc and 1(N) aq HCl
  2. washOrganic layer washed with 1(N) aq HCl (2×)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to light yellow viscous material (24.63 g, 94%)
  5. customThis material was used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-337927e2294b41c7ba3c1c1f19860c77
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691879B2

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