Sulfuric Acid → 5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinamide

HRID 1511122ノート

反応式

HRID 1511122 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][C:8]1[CH:9]=[C:10]([O:16][C:17]2[C:18]([CH3:24])=[N:19][N:20]([CH3:23])[C:21]=2[CH3:22])[C:11]([C:14]#[N:15])=[N:12][CH:13]=1.S(=O)(=O)(O)[OH:26].[OH-].[Na+]>O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][C:8]1[CH:9]=[C:10]([O:16][C:17]2[C:18]([CH3:24])=[N:19][N:20]([CH3:23])[C:21]=2[CH3:22])[C:11]([C:14]([NH2:15])=[O:26])=[N:12][CH:13]=1

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 674864015-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinonitrile

生成物 1

HCID 674856415-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinamide収率 89%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A flask was charged with 5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinonitrile (35.19 g, 88.1 mmol), and sulfuric acid (227.3 g, 2317 mmol) and stirred at ambient temperature overnight. Water (100 mL) was slowly added to the reaction which was cooled in an ice bath, then ice (150 g) was added. 40% NaOH was slowly added until the pH was about 12. The mixture was extracted ethyl acetate (750 mL×2), and dichloromethane (500 mL). The organic layers were dried over sodium sulfate and concentrated in vacuo to afford 5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinamide (27.69 g, 77.9 mmol, 89% yield).

後処理

  1. temperaturewas cooled in an ice bath
  2. extractionThe mixture was extracted ethyl acetate (750 mL×2), and dichloromethane (500 mL)
  3. dry with materialThe organic layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-033446f7a3a14ff3a7ccb2dd0b9f9d62
出典データセット
uspto-grants-2012_07
特許番号
US08212045B2

反応ノート

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