Potassium Carbonate → 5-formyl-2-(3-nitro-1H-1,2,4-triazol-1-yl)benzonitrile

HRID 1504708Notes

Reaction equation

HRID 1504708 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].C([O-])([O-])=O.[K+].[K+].[N+:18]([C:21]1[N:25]=[CH:24][NH:23][N:22]=1)([O-:20])=[O:19]>CN(C=O)C.O>[CH:10]([C:7]1[CH:8]=[CH:9][C:2]([N:23]2[CH:24]=[N:25][C:21]([N+:18]([O-:20])=[O:19])=[N:22]2)=[C:3]([CH:6]=1)[C:4]#[N:5])=[O:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27695822-Fluoro-5-formylbenzonitrileHCID 178526901HCID 178526901, compound

Product 1

HCID 866752155-formyl-2-(3-nitro-1H-1,2,4-triazol-1-yl)benzonitrileYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stiffing solution of 2-fluoro-5-formylbenzonitrile (0.5 g, 3.3 mmol) in DMF (25 mL) were added K2CO3 (0.68 g, 4.95 mmol) and 3-nitro-1,2,4 triazole (0.45 g, 4.2 mmol) and the resultant reaction mixture was stirred at ambient temperature for 14 h. After completion of reaction (TLC), the reaction mixture was diluted with water and extracted with EtOAc. The combined EtOAc layer was washed with water and brine then dried over Na2SO4 and concentrated under reduced pressure to afforded the title compound as a pale yellow solid (0.36 g, 45%): mp 170-172° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.12 (s, 1H), 9.61 (s, 1H), 8.69 (s, 1H), 8.45 (d, J=9.3 Hz, 1H), 8.23 (d, J=9.3 Hz, 1H); ESIMS m/z 242.3 ([M−H]−); IR (thin film) 2238, 1705, 1551, 1314 cm−1.

Workup

  1. customthe resultant reaction mixture
  2. customAfter completion of reaction (TLC)
  3. extractionextracted with EtOAc
  4. washThe combined EtOAc layer was washed with water and brine
  5. dry with materialthen dried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-78d04331418941d4a914e5aee6c44b2a
Source dataset
uspto-grants-2015_12
Patent number
US09215870B2

Reaction notes

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