Hydrochloric Acid → 5-Methyl[1,3]oxazolo[4,5-b]pyridine-2(3H)-thione

HRID 70144

반응식

HRID 70144 반응식
C([O-])=O.[NH4+].[N+:5]([C:8]1[C:13]([OH:14])=[CH:12][CH:11]=[C:10]([CH3:15])[N:9]=1)([O-])=O.[OH-].[K+].Cl.[C:19](=S)=[S:20]>CCO.[OH-].[OH-].[Pd+2]>[CH3:15][C:10]1[N:9]=[C:8]2[NH:5][C:19](=[S:20])[O:14][C:13]2=[CH:12][CH:11]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 848016-Methyl-2-nitropyridin-3-olHCID 2723923Ammonium formate

생성물 1

HCID 126642785-Methyl[1,3]oxazolo[4,5-b]pyridine-2(3H)-thione

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 702Ethanol용매2회

반응 조건

온도
70 °C

실험 절차

Ammonium formate (1.64 g, 26 mmol) was added to a suspension of Pd(OH)2 on carbon (˜20% Pd, 0.73 g, 1.0 mmol) and 2-nitro-3-hydroxy-6-methylpyridine (2.0 g, 13 mmol) in EtOH (20 mL). The reaction mixture was heated to 70° C. for 1 h at which point the reaction mixture was allowed to cool to rt and was filtered through Celite®. The filtrate was concentrated under reduced pressure, yielding a thick orangish oil. The material was dissolved in EtOH (25 mL) and potassium hydroxide (0.875 g, 15.6 mmol) and carbon disulfide (15 mL) were added. The reaction mixture was heated to reflux overnight. Upon cooling to rt, the reaction mixture was acidified with 1 N HCl, and the resulting solid was collected by filtration. The solid was washed with water (2×) and air dried followed by drying in a 35° C. vacuum oven. LC-MS: RT=5.58 min, [M+H]+=167.0.

후처리

  1. temperatureto cool to rt
  2. filtrationwas filtered through Celite®
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customyielding a thick orangish oil
  5. temperatureThe reaction mixture was heated
  6. temperatureto reflux overnight
  7. temperatureUpon cooling to rt
  8. filtrationthe resulting solid was collected by filtration
  9. washThe solid was washed with water (2×) and air
  10. customdried
  11. customby drying in a 35° C. vacuum oven

출처 및 근거

ORD 기록
ord-64982537af614bce91986c2fc8093296
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822472B2

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