Trifluoroacetic acid → HCID 5149609, compound

HRID 1475190Notes

Reaction equation

HRID 1475190 reaction equation
[C:1]1([C:7]2[O:11][C:10]([C:12]([NH:14][NH:15]C(OC(C)(C)C)=O)=[O:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]1([C:7]2[O:11][C:10]([C:12]([NH:14][NH2:15])=[O:13])=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86711881HCID 86711881, compound

Product 1

HCID 5149609HCID 5149609, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(5-phenylfuran-2-carbonyl)hydrazinecarboxylate (300 mg, 1 mmol) in DCM (10 mL), TFA (4.85 g, 50 mmol) was added dropwise. The mixture was stirred at RT overnight, then concentrated under reduced pressure and purified by silica gel column chromatography (EtOAc:Petroleum ether:TEA=50:50:1) to afford 5-phenylfuran-2-carbohydrazide as a light yellow solid (150 mg, 74%). MS (ES+) C11H10N2O2 requires: 202. found: 203 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by silica gel column chromatography (EtOAc:Petroleum ether:TEA=50:50:1)

Sources & evidence

ORD record
ord-72eb108d331b43a0bcdc332955d95964
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

Loading…