Pyridine → 5-(2-chloro-6-fluorophenyl)-2-(4-iodophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 508717Notes

Reaction equation

HRID 508717 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9](=[N:11][NH:12][C:13]1[CH:18]=[CH:17][C:16]([I:19])=[CH:15][CH:14]=1)[NH2:10].N1C=CC=CC=1.[C:26](Cl)(Cl)=[O:27]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:10][C:26](=[O:27])[N:12]([C:13]2[CH:18]=[CH:17][C:16]([I:19])=[CH:15][CH:14]=2)[N:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6371PhosgeneHCID 117965459HCID 117965459, compound

Product 1

HCID 1366448545-(2-chloro-6-fluorophenyl)-2-(4-iodophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 41.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The title a compound was prepared according to the procedure described in step-4 of Intermediate-1 using 2-chloro-6-fluoro-N′-(4-iodophenyl)benzene carbohydrazonamide (0.900 g, 2.31 mmol), pyridine (0.65 mL, 5.79 mmol), phosgene (2.50 mL, 4.63 mmol) and CHCl3 (20 mL). The obtained crude product was purified with column chromatography on silica gel eluting with 1.0% MeOH:DCM to afford 0.400 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 7.47 (t, J=9.0 Hz, 2H), 7.54-7.82 (m, 5H), 12.62 (s, 1H). MS (m/z): 414.25 (M−H)−.

Workup

  1. customThe title a compound was prepared
  2. customThe obtained crude product
  3. customwas purified with column chromatography on silica gel eluting with 1.0% MeOH

Sources & evidence

ORD record
ord-f91d892154244da8b1780d90543b311d
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

Loading…