Benzeneacetonitrile, 2-fluoro- → 3-(2-fluorophenyl)[1,2,3]triazolo[1,5-a]quinazolin-5(4H)-one

HRID 1250170Notes

Reaction equation

HRID 1250170 reaction equation
[Na].[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]#[N:11].[N:12]([C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=O)=[N+:13]=[N-:14]>C(O)C>[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10]2=[N:11][C:17](=[O:19])[C:16]3[C:15]([N:12]2[NH:13][N:14]=1)=[CH:23][CH:22]=[CH:21][CH:20]=3

Participants

5

Reactant 3

HCID 67592Benzeneacetonitrile, 2-fluoro-HCID 53255602-Azidobenzoic acidHCID 5360545Sodium

Product 1

HCID 32407283-(2-fluorophenyl)[1,2,3]triazolo[1,5-a]quinazolin-5(4H)-oneYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium (0.55 g, 24 mmol) was dissolved in dry ethanol (25 ml) at room temperature under nitrogen. 2-Fluorophenylacetonitrile (1.9 ml, 15 mmol) was added and the orange solution was stirred for 15 min, followed by dropwise addition of a solution of 2-azidobenzoic acid (1.97 g, 12.1 mmol) in diy ethanol (20 ml). The thick, white gel was stirred at room temperature for 45 min then refluxed for 18 h. Solvent was removed by evaporation and water (40 ml) was added. The yellow suspension was acidified with aqueous citric acid (1 M). The precipitate was collected, washed with water and dried in vacuo at room temperature to give 3-(2-fluorophenyl)-1,2,3-triazolo[1,5-α]quinazolin-5-one (3.38 g, 100%) as an off-white powder, m.p. 238-241° C. (DMF). Found: C, 64.33; H, 3.06; N, 20.29. C15H9FN4O requires C, 64.28; H, 3.24; N, 19.99%. δH (360 MHz; DMSO) 7.33-7.38 (2H, m), 7.46-7.55 (1H, m), 7.69-7.73 (2H, m), 8.02 (1H, ddd, J=9, 9 and 1), 8.24 (1H, dd, J=8 and 1), 8.38 (1H, d, J=8) and 12.40 (1H, br s); m/z (ES+) 821 (M+H+).

Workup

  1. stirringThe thick, white gel was stirred at room temperature for 45 min
  2. temperaturethen refluxed for 18 h
  3. customSolvent was removed by evaporation and water (40 ml)
  4. additionwas added
  5. customThe precipitate was collected
  6. washwashed with water
  7. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-0eb03b7e20664be6a257ae28548cc0c0
Source dataset
uspto-grants-2002_01
Patent number
US06337331B1

Reaction notes

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