Cyanamide → (1-{6-[Chloro(difluoro)methyl]pyridin-3-yl}ethyl)(methyl)-lambda4-sulfanylidenecyanamide

HRID 82329

Reaktionsgleichung

Reaktionsgleichung von HRID 82329
[Cl:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([S:11][CH3:12])[CH3:10])=[CH:5][N:4]=1.[N:15]#[C:16][NH2:17].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C1COCC1>[Cl:1][C:2]([F:13])([F:14])[C:3]1[N:4]=[CH:5][C:6]([CH:9]([S:11]([CH3:12])=[N:17][C:16]#[N:15])[CH3:10])=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 9864CyanamideHCID 12217721Iodo benzene diacetateHCID 592185952-[Chloro(difluoro)methyl]-5-[1-(methylthio)ethyl]pyridine

Produkt 1

HCID 24753361(1-{6-[Chloro(difluoro)methyl]pyridin-3-yl}ethyl)(methyl)-lambda4-sulfanylidenecyanamideAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-[chloro(difluoro)methyl]-5-[1-(methylthio)-ethyl]pyridine (E) (0.32 g, 1.35 mmol) and cyanamide (0.058 g, 1.35 mmol) in THF (7 mL) was added iodobenzene diacetate (0.44 g, 1.35 mmol) in one portion at 0° C. and the resulting mixture was stirred at this temperature for 1 hr and then at room temperature for 2 hr. The solvent was then removed under reduced pressure and the resulting mixture was dissolved in CH2Cl2, washed with half-saturated brine, dried over anhydrous Na2SO4, filtered, concentrated, and purified on silica gel using 50 percent acetone in hexane to give 0.175 g of (1-{6-[chloro-(difluoro)methyl]pyridin-3-yl}ethyl)(methyl)-λ4-sulfanylidenecyanamide (F) as light-yellow oil in 48 percent yield. 1H NMR (300 MHz, CDCl3) δ 8.71 (d, J=1.8 Hz, 1H), 7.91 (dd, J=8.4, 1.8 Hz, 1H) 7.78 (d, J=8.4 Hz, 1H), 4.42 (q, J=6.9 Hz, 1H), 2.64 (s, 3H), 1.92 (d, J=6.9 Hz, 3H); LC-MS: mass calcd for C10H10ClF2N3S [M+1]+ 278. Found 278.

Aufarbeitung

  1. waitat room temperature for 2 hr
  2. customThe solvent was then removed under reduced pressure
  3. dissolutionthe resulting mixture was dissolved in CH2Cl2
  4. washwashed with half-saturated brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified on silica gel using 50 percent acetone in hexane

Quellen und Nachweise

ORD-Eintrag
ord-51cf5689d3554ff581a9cc9cfcd8130e
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846717B2

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