Water → N-(6-Chloropyridin-2-yl)-2,2-dimethylpropanamide

HRID 751666

Reaktionsgleichung

Reaktionsgleichung von HRID 751666
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[N:3]=1.C(N(CC)CC)C.[CH3:16][C:17]([CH3:22])([CH3:21])[C:18](Cl)=[O:19].O>ClCCl>[Cl:8][C:4]1[N:3]=[C:2]([NH:1][C:18](=[O:19])[C:17]([CH3:22])([CH3:21])[CH3:16])[CH:7]=[CH:6][CH:5]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 2062462-Amino-6-chloropyridine

Produkt 1

HCID 13154248N-(6-Chloropyridin-2-yl)-2,2-dimethylpropanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-amino-6-chloropyridine (3.0 g, 23.3 mmol) in dichloromethane (45 mL) under argon was added triethylamine (4.10 mL, 29.2 mmol) and the reaction cooled to 0° C. (ice bath). A solution of trimethylacetyl chloride (3.16 mL, 25.7 mmol) in dichloromethane (10 mL) was added dropwise over 20 min before stirring for 30 min at 0° C. The reaction was brought up to rt and stirred for a further 5 h, then water (30 mL) was added. The organics were separated and washed with Na2CO3 solution (2×50 mL), dried,(MgSO4) and solvent removed in vacuo. Purification by column chromatography (SiO2, CH2Cl2) gave the title compound. m/z (ES+)=213.04 [M+H]+.

Aufarbeitung

  1. customwas brought up to rt
  2. stirringstirred for a further 5 h
  3. customThe organics were separated
  4. washwashed with Na2CO3 solution (2×50 mL), dried,(MgSO4) and solvent
  5. customremoved in vacuo
  6. customPurification by column chromatography (SiO2, CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-24890e84996c48479095b62ad5797443
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405210B2

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