Felbinac → N-(3-fluorophenyl)-2-(4-phenylphenyl)acetamide

HRID 874472Notes

Reaction equation

HRID 874472 reaction equation
S(Cl)(Cl)=O.[C:5]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=O)=[CH:7][CH:6]=1.[F:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25]>ClCCl.CN(C)C1C=CN=CC=1.O>[F:21][C:22]1[CH:23]=[C:24]([NH:25][C:12](=[O:14])[CH2:11][C:8]2[CH:7]=[CH:6][C:5]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][CH:9]=2)[CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 3

HCID 3332FelbinacHCID 97423-FluoroanilineHCID 24386Thionyl Chloride

Product 1

HCID 4853818N-(3-fluorophenyl)-2-(4-phenylphenyl)acetamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

Thionyl chloride (0.38 ml, 5.0 mmole) was added to an ice water cooled solution of 4-Biphenylacetic acid (0.2 g, 0.9 mmole) in 5 ml dichloromethane, solution allowed to warm to room temperature then heated under reflux for 1 hr, the solvent and excess thionyl chloride was evaporated under vacuum, the oil formed was redissolved in 5 ml dichloromethane followed by addition of 4-Dimethylaminopyridine (0.12 gm, 1.0 mmole) and 3-Fluoroaniline (0.11 gm, 1.0 mmole), stirred at room temperature over night, then the reaction mixture was diluted with 10 ml dichloromethane and 20 ml water, the organic layer washed with 1 N HCl, saturated NaHCO3 solution, and saturated NaCl solution, dried using Na2SO4 and evaporated dryness (0.2 gm, 72%), H1-NMR INOVA-500 (CDCl3) δ 3.805 (s, 2H), 6.815 (t, J=8.5 Hz, 1H), 7.068 (d, J=8.0 Hz, 1H), 7.218-7.284 (m, 2H), 7.380-7.499 (m, 6H) 7.620-7.664 (m, 4H). MS (m/z) 306.2 (M+H)+.

Workup

  1. temperaturethen heated
  2. temperatureunder reflux for 1 hr
  3. customthe solvent and excess thionyl chloride was evaporated under vacuum
  4. customthe oil formed
  5. washthe organic layer washed with 1 N HCl, saturated NaHCO3 solution, and saturated NaCl solution
  6. customdried
  7. customevaporated dryness (0.2 gm, 72%)

Sources & evidence

ORD record
ord-20508d95115e4e708a8bb2d2f9617803
Source dataset
uspto-grants-2015_03
Patent number
US08980890B2

Reaction notes

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