Aniline → Acetamide, 2-cyano-N-phenyl-

HRID 599504

反応式

HRID 599504 の反応式
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].P(Cl)(Cl)(Cl)(Cl)Cl.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>ClCCl>[C:1]([CH2:3][C:4]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:6])#[N:2]

参加物

6

反応物 4

HCID 6115AnilineHCID 9740Cyanoacetic acidHCID 10340Sodium CarbonateHCID 24819Phosphorus pentachloride

生成物 1

HCID 69296Acetamide, 2-cyano-N-phenyl-収率 82.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Cyanoacetic acid (1.0 g, 11.7 mmol) is added to a stirred suspension of PCl5 (2.4 g, 11.7 mmol) in dry dichloromethane (200 ml). The reaction mixture is heated to reflux and kept stirring for 30 min. After cooling to rt, aniline (1.07 ml, 11.7 mmol) is added dropwise and the reaction is stirred at reflux for additional 2 h, then cooled to 0° C. and neutralized by addition of aqueous saturated Na2CO3 solution. The precipitate is filtered off, washed with water and dried under high vacuum to give title compound (1.54 g) as a white solid in 82% yield: tR (LC-2) 1.50 min; ESI-MS(+): m/z 183.33 [M+Na]+ (calcd 160.17 for C9H8N2O).

後処理

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux
  3. stirringthe reaction is stirred
  4. temperatureat reflux for additional 2 h
  5. temperaturecooled to 0° C.
  6. filtrationThe precipitate is filtered off
  7. washwashed with water
  8. customdried under high vacuum

出典と根拠

ORDレコード
ord-beb61a672d1945c693a4116135063da8
出典データセット
uspto-grants-2011_03
特許番号
US07897788B2

関連ノート

読み込み中…