Cyanamide → HCID 21357925, Verbindung

HRID 1167832

Reaktionsgleichung

Reaktionsgleichung von HRID 1167832
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:13]=[C:14]=[S:15])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[N:16]#[C:17][NH2:18].O(C(C)(C)C)[K].Cl.Cl[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.C([Li])CCC>C(#N)C.C(O)(C)(C)C.O.C1COCC1>[N:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[C:27]1[S:15][C:14]([NH:13][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=2)=[N:16][C:17]=1[NH2:18]

Komponenten

9

Edukt 5

HCID 9864CyanamideHCID 23392Picolyl chloride hydrochlorideHCID 1189003,4,5-Trimethoxyphenyl isothiocyanateHCID 178418339ButyllithiumHCID 178418922HCID 178418922, Verbindung

Produkt 1

HCID 21357925HCID 21357925, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 22050040Acetonitrile tert-butanolLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

3,4,5-Trimethoxyphenyl isothiocynate (250 mg, 1.11 mmol, 1 equiv.) and cyanamide (56 mg, 1.33 mmol, 1.2 equiv.) were taken up in acetonitrile-tert-butanol (1:1, 10 mL) at 23° C. To this was added KO-t-Bu (286 mg, 2.55 mmol, 2.3 equiv.) and 2-chloromethylpyridine hydrochloride (182 mg, 1.11 mmol, 1.00 equiv.). The reaction mixture was allowed to stir for 1.5 h at 23° C. The mixture was diluted with water (20 mL) and the white solids were filtered, washed with ether and dried (257 mg). The dried residue (60 mg, 0.167 mmol, 1.00 equiv.) was dissolved in THF (3 mL), cooled to −78° C. and was treated with n-butyllithium (0.261 mL, 1.6 M, 2.5 equiv.). The mixture was allowed to warm to 23° C., was quenched with saturated sodium bicarbonate, and organics were extracted into ethyl acetate. The concentrated residue was purified by silica gel chromatography (ethyl acetate/hexane: 1:1, 48.3 mg, 80%).

Aufarbeitung

  1. filtrationthe white solids were filtered
  2. washwashed with ether
  3. customdried (257 mg)
  4. temperaturecooled to −78° C.
  5. temperatureto warm to 23° C.
  6. customwas quenched with saturated sodium bicarbonate
  7. extractionorganics were extracted into ethyl acetate
  8. customThe concentrated residue was purified by silica gel chromatography (ethyl acetate/hexane: 1:1, 48.3 mg, 80%)

Quellen und Nachweise

ORD-Eintrag
ord-2cfece655d2e4757a83b8b57afa54f42
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06620828B2

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