Hydrochloric Acid → 1-(5-Amino-2-chloro-4-fluorophenyl)-3-(2-propynyl)-s-triazine-2,4,6-(1H,3H,5H)-trione

HRID 52427Notes

Reaction equation

HRID 52427 reaction equation
[Cl:1][C:2]1[C:11]([N:12]2[C:17](=[O:18])[NH:16][C:15](=[O:19])[N:14]([CH2:20][C:21]#[CH:22])[C:13]2=[O:23])=[CH:10][C:5]([NH:6]C(=O)C)=[C:4]([F:24])[CH:3]=1.Cl.C(OCC)(=O)C.[OH-].[Na+]>C(O)C>[NH2:6][C:5]1[C:4]([F:24])=[CH:3][C:2]([Cl:1])=[C:11]([N:12]2[C:17](=[O:18])[NH:16][C:15](=[O:19])[N:14]([CH2:20][C:21]#[CH:22])[C:13]2=[O:23])[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 569836604'-Chloro-2'-fluoro-5'-[hexahydro-2,4,6trioxo-3(2-propynyl)-s-triazin-1-yl]acetanilide

Product 1

HCID 196907381-(5-Amino-2-chloro-4-fluorophenyl)-3-(2-propynyl)-s-triazine-2,4,6-(1H,3H,5H)-trioneYield 82.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4'-chloro-2'-fluoro-5'-[hexahydro-2,4,6trioxo-3(2-propynyl)-s-triazin-1-yl]acetanilide (3.00 g, 8.5 mmol), and 3N hydrochloric acid (25 mL) in ethanol (50 mL) is refluxed for 3 hours, cooled to room temperature, and poured into ethyl acetate. 3N sodium hydroxide solution (25 mL) is added to the organic solution, and the phases are separated. The organic phase is washed sequentially with saturated sodium hydrogen carbonate solution and brine, and concentrated in vacuo to give the title product as a beige solid (2.17 g, mp 118°-121° C.).

Workup

  1. temperatureis refluxed for 3 hours
  2. customthe phases are separated
  3. washThe organic phase is washed sequentially with saturated sodium hydrogen carbonate solution and brine
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6fef3638ae7f4168b85dd4b46de40edf
Source dataset
uspto-grants-1997_04
Patent number
US05616706

Reaction notes

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