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

HRID 1511100ノート

反応式

HRID 1511100 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-ce124c51c1034149a0a68e360f272b66
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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