Acetic Acid → 1-Methyl-1,5-dihydro-imidazo[4,5-c]pyridine-4-thione

HRID 362564

Reaktionsgleichung

Reaktionsgleichung von HRID 362564
Cl[C:2]1[C:7]2[N:8]=[CH:9][N:10]([CH3:11])[C:6]=2[CH:5]=[CH:4][N:3]=1.O.[SH2:13].[Na].O.C(O)(=O)C>CN(C)C=O>[CH3:11][N:10]1[C:6]2[CH:5]=[CH:4][NH:3][C:2](=[S:13])[C:7]=2[N:8]=[CH:9]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 962WaterHCID 9487924-chloro-1-methyl-1H-imidazo(4,5-c)pyridineHCID 53442613Sodium hydrogen sulfide hydrate

Produkt 1

HCID 193535981-Methyl-1,5-dihydro-imidazo[4,5-c]pyridine-4-thioneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

4.00 g (23.9 mmol) of 4-chloro-1-methyl-1H-imidazo[4,5-c]pyridine in 27 ml of dimethylformamide were stirred at 115° C. for 18 hours with 8.10 g (95.6 mmol) of sodium hydrogen sulphide hydrate. After cooling the mixture was treated with 110 ml of water, adjusted to pH 4 with acetic acid and stirred at 5° C. while cooling with ice for 15 min. The precipitate was filtered off and washed with water. After drying there were obtained 3.73 g (95%) of 1-methyl-1,5-dihydro-imidazo[4,5-c]pyridine-4-thione as white crystals with m.p. >300° C.

Aufarbeitung

  1. temperatureAfter cooling the mixture
  2. temperaturewhile cooling with ice for 15 min
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customAfter drying there

Quellen und Nachweise

ORD-Eintrag
ord-505a70ca758b4c6cae28240203f97f47
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05869500

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