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

HRID 599504

Reaction equation

HRID 599504 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-beb61a672d1945c693a4116135063da8
Source dataset
uspto-grants-2011_03
Patent number
US07897788B2

Linked notes

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