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

HRID 43150Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 43150
[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-a0539809da9a4c12b09466ef0ec3c822
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536175B2

Notizen zur Reaktion

Wird geladen…