Hydrochloric Acid → 6-[(1,1-Dimethylethyl)thio]-3-pyridinemethanamine

HRID 2041509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2041509
[C:1]([S:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].Cl>C1COCC1.CO>[NH2:11][CH2:10][C:9]1[CH:12]=[CH:13][C:6]([S:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[N:7][CH:8]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 284131906-(Tert-butylsulfanyl)pyridine-3-carbonitrile

Produkt 1

HCID 435287746-[(1,1-Dimethylethyl)thio]-3-pyridinemethanamineAusbeute 61,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Use a method similar to the General Procedure 6-5 to react 6-(tert-butylthio)nicotinonitrile (4.4 g, 22.7 mmol) in anhydrous THF (25 mL) with 1M BH3-THF complex in THF (25 mL, 25 mmol). Add 5M aqueous HCl (10 mL) cautiously and stir the mixture overnight at room temperature. Extract into EtOAc, wash with brine, dry over MgSO4 and concentrate in vacuo to give an orange solid. Dissolve the crude mixture in methanol and filter through an SCX column eluting with methanol followed by 3M ammonia in methanol to obtain the title compound (2.74 g, 61%). MS (ES+) m/z: 197 (M+H)+.

Aufarbeitung

  1. extractionExtract into EtOAc
  2. washwash with brine
  3. dry with materialdry over MgSO4
  4. concentrationconcentrate in vacuo
  5. customto give an orange solid
  6. filtrationfilter through an SCX column
  7. washeluting with methanol

Quellen und Nachweise

ORD-Eintrag
ord-9398ab867daa4b84b0161aeff82f1573
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580780B2

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