Hydrazine hydrate (1:1) → 6-(4-Chlorophenyl)-4,5-dihydro-1,2,4-triazin-3-one

HRID 889822Notes

Reaction equation

HRID 889822 reaction equation
O.[NH2:2][NH2:3].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH2:12][N:13]2C(=O)CS[C:14]2=[O:19])=[CH:7][CH:6]=1>CO>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:12][NH:13][C:14](=[O:19])[NH:2][N:3]=2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 12061653-[2-(4-Chlorophenyl)-2-oxoethyl]-1,3-thiazolidine-2,4-dione

Product 1

HCID 691185446-(4-Chlorophenyl)-4,5-dihydro-1,2,4-triazin-3-oneYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrazine hydrate (8.0 g, 160 mmol) and 19.55 g of 3-(2-(4-chlorophenyl)-2-oxo-ethyl)-thiazolidine-2,4-dione in 100 mL of methanol were stirred at room temperature over a weekend, then refluxed for 8 hours. The reaction mixture was cooled and the solids were filtered, washed with methanol and dried to give 9.06 g of white solid 6-(4-chlorophenyl)-4,5-dihydro-1,2,4-triazin-3-one (57% yield).

Workup

  1. temperaturerefluxed for 8 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe solids were filtered
  4. washwashed with methanol
  5. customdried

Sources & evidence

ORD record
ord-e33b46ff6cfa452bbc392bf6c6e9d309
Source dataset
uspto-grants-2006_02
Patent number
US06995157B2

Reaction notes

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