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

HRID 70144

反応式

HRID 70144 の反応式
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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 702Ethanol溶媒2 回

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-64982537af614bce91986c2fc8093296
出典データセット
uspto-grants-2014_09
特許番号
US08822472B2

関連ノート

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