Benzene → HCID 178523136, compound

HRID 1444706Notes

Reaction equation

HRID 1444706 reaction equation
[C:1]([C:3]1[CH:17]=[CH:16][C:6]([CH2:7][CH2:8][NH:9][C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])=[CH:5][CH:4]=1)#[N:2].C1C=CC=CC=1.[CH:24]([NH:26][NH2:27])=O>CCO.N1C=CC=CC=1>[N:26]1[N:27]=[C:1]([C:3]2[CH:4]=[CH:5][C:6]([CH2:7][CH2:8][NH:9][C:10](=[O:15])[C:11]([F:12])([F:13])[F:14])=[CH:16][CH:17]=2)[NH:2][CH:24]=1

Participants

6

Reactant 3

HCID 241BenzeneHCID 12229HydrazinecarboxaldehydeHCID 58597276HCID 58597276, compound

Product 1

HCID 178523136HCID 178523136, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

(N-(4-cyanophenethyl)-2,2,2-trifluoroacetamide (0.61 g, 2.52 mmol) was azeotroped with benzene and was dissolved in 10 mL of anhydrous EtOH. To this solution dry HCl was bubbled though for 90 min at 0 C. The solvent was evaporated to dryness under high vacuum to give a yellow solid. This yellow solid and formohydrazide (151 mg, 2.52 mmol) was dissolved in 10 mL of dry pyridine and the resulting solution was refluxed for 2 h. After cooling to RT, pyridine was evaporated and the residue was treated with 5% HCl, extracted with EtOAc, dried over Na2SO4, filtered, and evaporated to dryness. Flash chomatography (SiO2, EtOAc/DCM=1:1 to Dcm/MeOH=10:1) afforded N-(4-(4H-1,2,4-triazol-3-yl)phenethyl)-2,2,2-trifluoroacetamide as a white solid.

Workup

  1. customTo this solution dry HCl was bubbled though for 90 min at 0 C
  2. customThe solvent was evaporated to dryness under high vacuum
  3. customto give a yellow solid
  4. temperaturethe resulting solution was refluxed for 2 h
  5. custompyridine was evaporated
  6. additionthe residue was treated with 5% HCl
  7. extractionextracted with EtOAc
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-268104e373a24803a8718b5123111943
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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