Triethylamine → tert-butyl N-(2-chloropyridin-4-yl)carbamate

HRID 1092281Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1092281
[C:1](OC([O-])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN(C1C=CC=CN=1)C.[NH2:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]([Cl:28])[CH:23]=1.C(N(CC)CC)C>ClCCl.O>[Cl:28][C:24]1[CH:23]=[C:22]([NH:21][C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[CH:27]=[CH:26][N:25]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 844322-Chloropyridin-4-amineHCID 22064466Tert-butyldicarbonate

Produkt 1

HCID 21858447tert-butyl N-(2-chloropyridin-4-yl)carbamateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

1.69 g (7.78 mmol, 1 eq) of tert-butyl dicarbonate dissolved in 50 ml of dichloromethane, in the presence of 95 mg of dimethylaminopyridine, are added to a solution of 1 g (7.78 mmol, 1 eq) of 4-amino-2-chloropyridine in 30 mL of dichloromethane in the presence of 1.19 mL (1.19 mmol, 1.1 eq) of triethylamine. The reaction mixture is stirred overnight at room temperature. The reaction is stopped by adding 100 ml of water and is then extracted with dichloromethane. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (70/30 to 50/50 heptane/ethyl acetate). The oil obtained is crystallized from pentane. 1.40 g of tert-butyl (2-chloropyrid-4-yl)carbamate are obtained. Yield=80%.

Aufarbeitung

  1. extractionis then extracted with dichloromethane
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated off
  4. customthe residue is then chromatographed on silica gel (70/30 to 50/50 heptane/ethyl acetate)
  5. customThe oil obtained
  6. customis crystallized from pentane

Quellen und Nachweise

ORD-Eintrag
ord-7ff335cb7e2243f9a969bfa6844ecf0c
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129416B2

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