Trifluoroacetic acid → HCID 66651666, compound

HRID 419851Notes

Reaction equation

HRID 419851 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1.[CH3:16][C:17]1O[C:20]([C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)=[N:19][N:18]=1>O1CCCC1>[Cl:8][C:9]1[CH:15]=[CH:14][C:12]([N:13]2[C:17]([CH3:16])=[N:18][N:19]=[C:20]2[C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 78124-ChloroanilineHCID 6037184-(5-Methyl-1,3,4-oxadiazol-2-yl)benzonitrile

Product 1

HCID 66651666HCID 66651666, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trifluoroacetic acid (600 μl, 8.1 mmol) was added to a suspension of 4-chloroaniline (2.1 g, 16.2 mmol) and 4-(5-methyl-1,3,4-oxadiazol-2-yl)benzonitrile (Journal für Praktische Chemie, 1994; 336(8); 678-85) (3.0 g, 16.2 mmol) in tetrahydrofuran (50 mL) and the reaction was heated at reflux for 22 hours. The cooled mixture was partitioned between ethyl acetate (300 mL) and 20% aqueous 0.88 ammonia (120 mL), and then the layers were separated. The organic phase was dried over MgSO4 and evaporated under reduced pressure. The residue was triturated with ether and a minimum volume of ethyl acetate to afford the title compound as a white crystalline solid, 2.82 g.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 22 hours
  3. customThe cooled mixture was partitioned between ethyl acetate (300 mL) and 20% aqueous 0.88 ammonia (120 mL)
  4. customthe layers were separated
  5. dry with materialThe organic phase was dried over MgSO4
  6. customevaporated under reduced pressure
  7. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-9d2d9efbc8f54ffcaa2e284c3152e74f
Source dataset
uspto-grants-2012_01
Patent number
US08093400B2

Reaction notes

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