Triethylamine → (6-Methyl-5-nitropyridin-2-yl)methyl methanesulfonate

HRID 1811590Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1811590
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C1COCC1>[CH3:20][S:21]([O:9][CH2:8][C:6]1[CH:5]=[CH:4][C:3]([N+:10]([O-:12])=[O:11])=[C:2]([CH3:1])[N:7]=1)(=[O:23])=[O:22]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 24776197(6-Methyl-5-nitropyridin-2-yl)methanol

Produkt 1

HCID 58671603(6-Methyl-5-nitropyridin-2-yl)methyl methanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(6-Methyl-5-nitropyridin-2-yl)methanol (12 g, 71 mmol), and triethylamine (9.4 g, 93 mmol) in THF (300 mL) was chilled in an ice bath to 10° C. and methanesulfonyl chloride (9.0 g, 79 mmol) was added dropwise and the solution was stirred for one hour, then filtered to remove triethylamine HCl, and the solvent was removed under reduced pressure on the rotovap (with the bath temperature at 35° C.) and (6-methyl-5-nitropyridin-2-yl)methyl methanesulfonate (17 g, 97%), a brown oil which was directly used as such. 1HNMR (CDCl3, 400 MHz) δ 2.87 (s, 3H), 3.16 (s, 3H), 5.83 (s, 2H), 7.55 (d, J=8.34, 1H), 8.38 (d, J=8.34, 1H); Exact mass calculated for C8H10N2O5: 246.03. found: 247.10 MS m/z (MH+).

Aufarbeitung

  1. filtrationfiltered
  2. customto remove triethylamine HCl
  3. customthe solvent was removed under reduced pressure on the rotovap (with the bath temperature at 35° C.) and (6-methyl-5-nitropyridin-2-yl)methyl methanesulfonate (17 g, 97%)

Quellen und Nachweise

ORD-Eintrag
ord-7f9f710e938c4194960d34c57773d03c
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362248B2

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