Citric Acid → HCID 178518573, compound

HRID 1581627Notes

Reaction equation

HRID 1581627 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)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C.O>[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[N:13][N:12]2[C:15]3[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:17](=[O:19])[NH:11][C:10]=12

Participants

7

Reactant 4

HCID 311Citric AcidHCID 67592Benzeneacetonitrile, 2-fluoro-HCID 53255602-Azidobenzoic acidHCID 5360545Sodium

Product 1

HCID 178518573HCID 178518573, compoundYield 108.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Sodium metal (1.4 g, 60 mmol) was dissolved in ethanol (100 ml) at room temperature under nitrogen. 2-Fluorophenylacetonitrile (3.85 ml, 30 mmol) was added, followed by the dropwise addition of a solution of 2-azidobenzoic acid (4.71 g, 29 mmol) in ethanol (60 ml). The thick white suspension was refluxed for 18 h then cooled and poured into water (800 ml). The mixture was acidified to pH 3-4 with aqueous 1M citric acid and the precipitated solid was collected. The solid was washed with diethyl ether (20 ml) and dried in vacuo to give 3-(2-fluorophenyl)-[1,2,3]triazolo[1,5-α]quinazolin-5(4H)-one (8.81 g, 100%), 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. temperatureThe thick white suspension was refluxed for 18 h
  2. temperaturethen cooled
  3. customthe precipitated solid was collected
  4. washThe solid was washed with diethyl ether (20 ml)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-570561ea2ecf476781f14800d7234e2e
Source dataset
uspto-grants-2004_05
Patent number
US06730681B2

Reaction notes

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