Pyridine → HCID 86711474, compound

HRID 517528Notes

Reaction equation

HRID 517528 reaction equation
[OH:1]/[N:2]=[C:3](/[NH2:15])\[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:6][CH:5]=1.N1C=CC=CC=1.Cl[C:23](=O)[C:24]([O:26][CH2:27][CH3:28])=[O:25]>C(Cl)(Cl)Cl>[F:14][C:11]([F:13])([F:12])[O:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]2[N:15]=[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[O:1][N:2]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 20884Ethoxalyl chlorideHCID 5702530n-Hydroxy-4-trifluoromethoxy-benzamidine

Product 1

HCID 86711474HCID 86711474, compoundYield 109.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of (E)-N′-hydroxy-4-(trifluoromethoxy)benzimidamide (3.0 g, 13.6 mmol) and pyridine (1.6 g, 20.4 mmol) in CHCl3 (20 mL), ethyl 2-chloro-2-oxoacetate (2.2 g, 16.4 mmol) was added slowly at 0° C. The mixture was stirred at reflux for 3 h, and then concentrated to give the crude product, which was purified by silica gel column chromatography (Petroleum ether:EtOAc=10:1) to give ethyl 3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carboxylate as a white solid (4.5 g, 82%). MS (ES+) C12H9F3N2O4 requires: 302 found: 303[M+H]+.

Workup

  1. temperatureat reflux for 3 h
  2. concentrationconcentrated
  3. customto give the crude product, which
  4. customwas purified by silica gel column chromatography (Petroleum ether:EtOAc=10:1)

Sources & evidence

ORD record
ord-091458ca6ee34ed6bd6ecb98cd144b32
Source dataset
uspto-grants-2015_08
Patent number
US09115120B2

Reaction notes

Loading…