Water → N-(4-Chloro-3-cyanophenyl)acetamide

HRID 538116Notes

Reaction equation

HRID 538116 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:17])=[C:13]([CH:16]=1)[C:14]#[N:15].C1(C)C=CC=CC=1.O>CCOC(C)=O>[Cl:17][C:12]1[CH:11]=[CH:10][C:9]([NH:8][C:5](=[O:7])[CH3:6])=[CH:16][C:13]=1[C:14]#[N:15]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 7918Acetic AnhydrideHCID 109972345-Amino-2-chlorobenzonitrile

Product 1

HCID 25638344N-(4-Chloro-3-cyanophenyl)acetamideYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Acetic anhydride (2.79 mL, 29.5 mmol), 5-amino-2-chloro-benzonitrile (3.00 g, 19.7 mmol), N,N-dimethylaminopyridine (0.241 g, 1.97 mmol), and toluene (50 mL) were combined and heated to reflux for 1.5 h. The reaction mixture was cooled, and water and EtOAc (150 mL) were added. The solid remaining in the mixture was collected and set aside. The aqueous layer was extracted once more with EtOAc, and the combined layers were washed with brine. The reserved precipitate was then dissolved in EtOAc, which was washed with brine. All organic layers were combined, dried, filtered, and concentrated. The residue was triturated with DCM/hexanes to yield the titled compound (3.52 g, 92% yield). This compound did not yield MS data. 1H NMR (400 MHz, CDCl3): 7.92 (d, J=1.0 Hz, 1H), 7.57 (dd, J=2.1, 1.2 Hz, 2H), 2.17 (s, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1.5 h
  3. temperatureThe reaction mixture was cooled
  4. customwas collected
  5. extractionThe aqueous layer was extracted once more with EtOAc
  6. washthe combined layers were washed with brine
  7. dissolutionThe reserved precipitate was then dissolved in EtOAc
  8. washwhich was washed with brine
  9. customdried
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was triturated with DCM/hexanes

Sources & evidence

ORD record
ord-26be471201f8452aa5e70931757b1e14
Source dataset
uspto-grants-2014_10
Patent number
US08865713B2

Reaction notes

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