Potassium Carbonate → 2-(5-Bromo-2-cyano-3-fluorophenylamino)acetamide

HRID 1182827Notes

Reaction equation

HRID 1182827 reaction equation
[Br:1][C:2]1[CH:9]=[C:8](F)[C:5]([C:6]#[N:7])=[C:4]([F:11])[CH:3]=1.Cl.[NH2:13][CH2:14][C:15]([NH2:17])=[O:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([C:6]#[N:7])=[C:8]([NH:13][CH2:14][C:15]([NH2:17])=[O:16])[CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2723639Glycinamide hydrochlorideHCID 27569164-Bromo-2,6-difluorobenzonitrile

Product 1

HCID 581184952-(5-Bromo-2-cyano-3-fluorophenylamino)acetamideYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

12.6 (58.3 mmol) 4-bromo-2,6-difluorobenzonitrile, 6.8 g (61.5 mmol) glycinamide hydrochloride and 16.1 g (116.5 mmol) K2CO3 were suspended in 50 ml DMF and heated at 70° C. for 18 h. Having cooled down to room temperature, the solvent was concentrated and water was added. The resulting precipitate was sucked off and washed with water. 13.3 g (84%) 2-(5-bromo-2-cyano-3-fluorophenylamino)acetamide was obtained. ESI-MS [m/z]: 272, 274 [M+H]+

Workup

  1. temperatureHaving cooled down to room temperature
  2. concentrationthe solvent was concentrated
  3. additionwater was added
  4. washwashed with water

Sources & evidence

ORD record
ord-e1cb3601729e42329260fca4e330e510
Source dataset
uspto-grants-2014_03
Patent number
US08664233B2

Reaction notes

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