Hydrochloric Acid → 6-(4-Chlorophenyl)-1,2,4-triazin-3-one

HRID 889823Notes

Reaction equation

HRID 889823 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][NH:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[N+](C1C=C(S([O-])(=O)=O)C=CC=1)([O-])=O.[Na+].[OH-].[Na+].Cl>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[N:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 31389Sodium 3-nitrobenzenesulfonateHCID 691185446-(4-Chlorophenyl)-4,5-dihydro-1,2,4-triazin-3-one

Product 1

HCID 222487986-(4-Chlorophenyl)-1,2,4-triazin-3-oneYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.64 g (17.4 mmol) of 6-(4-chlorophenyl)-4,5-dihydro-1,2,4-triazin-3-one, 4.0 g of sodium m-nitrobenzene sulfonate (17.8 mmol), 6.0 g of 50% sodium hydroxide (75.2 mmol) and 160 mL of water were refluxed overnight. The reaction mixture was cooled, then 1N aqueous HCl was added until the pH was slightly acidic to paper. The product was filtered, washed with water and dried to give 3.0 g of 6-(4-chlorophenyl)-1,2,4-triazin-3-one, which was used without further purification.

Workup

  1. temperaturewere refluxed overnight
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe product was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-9d533606d6fe4d94b682627da06b647e
Source dataset
uspto-grants-2006_02
Patent number
US06995157B2

Reaction notes

Loading…