Sodium Hydroxide → 3-(2-Ethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-amine

HRID 1523637ノート

反応式

HRID 1523637 の反応式
[CH2:1]([C:3]1[C:8]([O:9][C:10]2[C:11](C(N)=O)=[N:12][CH:13]=[C:14]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:15]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2].Br[N:27]1C(=O)CCC1=O.[OH-].[Na+]>CO.O.[NH4+].[Cl-]>[CH2:1]([C:3]1[C:8]([O:9][C:10]2[C:11]([NH2:27])=[N:12][CH:13]=[C:14]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:15]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2]

参加物

7

反応物 3

HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 674861443-(2-Ethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinamide

生成物 1

HCID 674859303-(2-Ethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-amine収率 80.6%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒2 回HCID 25517Ammonium Chloride溶媒

実験手順

3-(2-Ethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinamide (71 g, 201 mmol) was dissolved in MeOH (1 L). 1-Bromopyrrolidine-2,5-dione (46.6 g, 262 mmol) was added and the reaction was stirred at ambient temperature for 5 minutes and then cooled in an ice bath. Sodium hydroxide (41.9 g, 1048 mmol) dissolved in water (200 mL) was added slowly and the reaction was stirred at ambient temperature for 1 hour, refluxed for 8 hours and then cooled to ambient temperature overnight. The reaction was diluted with 2.5 L water and 0.5 L NH4Cl and stirred for 30 minutes. The precipitate was filtered and dried to afford 3-(2-ethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-amine (52.6 g, 162 mmol, 80.5% yield) as a tan solid.

後処理

  1. temperaturecooled in an ice bath
  2. additionwas added slowly
  3. stirringthe reaction was stirred at ambient temperature for 1 hour
  4. temperaturerefluxed for 8 hours
  5. temperaturecooled to ambient temperature overnight
  6. stirringstirred for 30 minutes
  7. filtrationThe precipitate was filtered
  8. customdried

出典と根拠

ORDレコード
ord-065b55536159416999d011f6345c9079
出典データセット
uspto-grants-2015_07
特許番号
US09079890B2

反応ノート

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