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

HRID 599504

반응식

HRID 599504 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-beb61a672d1945c693a4116135063da8
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897788B2

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