Sodium Hydroxide → S-Pyridin-2-yl hexanethioate

HRID 23305

Reaktionsgleichung

Reaktionsgleichung von HRID 23305
[C:1](Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[SH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[OH-].[Na+]>C(Cl)Cl>[C:1](=[O:7])([S:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 67340Hexanoyl chlorideHCID 178418616HCID 178418616, Verbindung

Produkt 1

HCID 12585772S-Pyridin-2-yl hexanethioateAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Following a general procedure (Rao et al., J. Org. Chem. 2000, 65: 1084), to a solution of n-hexanoyl chloride (6.73 g, 50.0 mmol) in CH2Cl2 (200 mL) was added 2-mercaptopyridine (5.55 g, 50.0 mmol) in portions as a solid during 5 min. The resulting mixture was stirred for 1 h, then 2 N NaOH (50 mL) was added. The organic phase was isolated, washed (water), dried (Na2SO4) and concentrated to afford a yellow oil. The oil was distilled bulb-to-bulb (110-120° C./0.03 mmHg) to afford a pale yellow oil (9.24 g, 88%): 1H NMR δ 0.89 (m, 3H), 1.35 (m, 4H), 1.73 (m, 2H), 2.69 (m, 2H), 7.29 (m, 1H), 7.60-7.76 (m, 2H), 8.62 (m, 1H); 13C NMR δ 13.7, 22.1, 24.9, 30.9, 44.0, 123.3, 129.9, 136.9, 150.2, 151.5, 196.4. Anal. Calcd for C11H15NOS: C, 63.12; H, 7.22; N, 6.69. Found: C, 63.02; H, 7.24; N, 6.74.

Aufarbeitung

  1. customThe organic phase was isolated
  2. washwashed (water)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto afford a yellow oil
  6. distillationThe oil was distilled bulb-to-bulb (110-120° C./0.03 mmHg)

Quellen und Nachweise

ORD-Eintrag
ord-305aec3451ef41059abc931c50c285af
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849730B2

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