Cyanoacetic acid → 2-cyano-N-[4-(pyridin-4-ylmethyl)phenyl]acetamide

HRID 1025441

反応式

HRID 1025441 の反応式
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].C(Cl)(=O)C(Cl)=O.[OH-].[Na+].[N:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]2[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=2)=[CH:17][CH:16]=1>ClCCl.CN(C=O)C>[C:1]([CH2:3][C:4]([NH:26][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][C:18]2[CH:17]=[CH:16][N:15]=[CH:20][CH:19]=2)=[CH:28][CH:27]=1)=[O:6])#[N:2]

参加物

7

反応物 4

HCID 9740Cyanoacetic acidHCID 14798Sodium Hydroxide2 回HCID 65578Oxalyl chlorideHCID 3071584-[(Pyridin-4-yl)methyl]aniline

生成物 1

HCID 712387662-cyano-N-[4-(pyridin-4-ylmethyl)phenyl]acetamide収率 52.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

Under ice-cooling, to a mixture of 18.0 g of cyanoacetic acid and 25 mL of oxalyl chloride were added 0.07 mL of DMF and 10 mL of dichloromethane, followed by stirring at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and then to the residue was added toluene, followed by further concentrating under reduced pressure. This procedure was repeated and excess hydrogen chloride and oxalyl chloride were removed. A mixture of the obtained crude product and 50 mL of dichloromethane was added to a mixture of 80 mL of a 1 M aqueous sodium hydroxide solution, 300 mL of dichloromethane, and 14.3 g of 4-(pyridin-4-ylmethyl)aniline under ice-cooling. During mixing the reagent, a 1 M aqueous sodium hydroxide solution was added on time to adjust the reaction solution to be kept alkaline. After stirring at room temperature for 30 minutes, the organic layer was collected by separation and the aqueous layer was extracted with dichloromethane. The combined organic layer was dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. The obtained residue was recrystallized from ethanol to obtain 10.2 g of 2-cyano-N-[4-(pyridin-4-ylmethyl)phenyl]acetamide as a pale yellow solid.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the residue was added toluene
  3. concentrationby further concentrating under reduced pressure
  4. customexcess hydrogen chloride and oxalyl chloride were removed
  5. additionA mixture of the
  6. customobtained crude product and 50 mL of dichloromethane
  7. temperaturecooling
  8. additionDuring mixing the reagent
  9. stirringAfter stirring at room temperature for 30 minutes
  10. customthe organic layer was collected by separation
  11. extractionthe aqueous layer was extracted with dichloromethane
  12. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  13. customthe solvent was evaporated under reduced pressure
  14. customThe obtained residue was recrystallized from ethanol

出典と根拠

ORDレコード
ord-c2033950befa48bb89b1b6fcf86c4c8a
出典データセット
uspto-grants-2014_05
特許番号
US08729068B2

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