Triethylamine → Methanesulfonic acid 5-nitro-pyridin-2-ylmethyl ester

HRID 2409713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2409713
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=[O:4])=[O:3].[N+:10]([C:13]1[CH:14]=[CH:15][C:16]([CH2:19]O)=[N:17][CH:18]=1)([O-:12])=[O:11].C(N(CC)CC)C>C(Cl)Cl>[N+:10]([C:13]1[CH:14]=[CH:15][C:16]([CH2:19][O:5][S:2]([CH3:1])(=[O:4])=[O:3])=[N:17][CH:18]=1)([O-:12])=[O:11]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 20583228(5-Nitropyridin-2-yl)methanol

Produkt 1

HCID 86641144Methanesulfonic acid 5-nitro-pyridin-2-ylmethyl esterAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

Methanesulfonic anhydride (1.79 g, 10.3 mmol, 1.1 equiv) was added portionwise to a cold (5° C.) mixture of (5-nitro-pyridin-2-yl)-methanol (Step 112.4) (1.44 g, 9.4 mmol) and triethylamine (1.57 mL, 11.3 mmol, 1.2 equiv) in DCM (20 mL), under an argon atmosphere. The reaction mixture was allowed to stir for 0.5 h at 5° C., quenched with H2O and extracted with DCM. The organic phase was washed with H2O, dried (Na2SO4), filtered and concentrated to provide 2.16 g of the title compound as a brown solid: ESI-MS: 231.1 [M−H]−; tR=2.85 min (System 1).

Aufarbeitung

  1. customquenched with H2O
  2. extractionextracted with DCM
  3. washThe organic phase was washed with H2O
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-86ef842a18b44933b333f4d10a654ac0
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815901B2

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