Hydrochloric Acid → 2-[4-(4-acetylbenzyl)-3,5-dichlorophenyl]-4,5-dihydro-1,2,4-triazin-3(2H)-one

HRID 1604317Notes

Reaction equation

HRID 1604317 reaction equation
[C:1]([C:4]1[CH:36]=[CH:35][C:7]([CH2:8][C:9]2[C:14]([Cl:15])=[CH:13][C:12]([N:16]([C:25]([NH:27][CH2:28][CH:29](OC)OC)=[O:26])[N:17]=CC3C=CC=CC=3)=[CH:11][C:10]=2[Cl:34])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].Cl>C(OCC)(=O)C>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:9]2[C:14]([Cl:15])=[CH:13][C:12]([N:16]3[C:25](=[O:26])[NH:27][CH2:28][CH:29]=[N:17]3)=[CH:11][C:10]=2[Cl:34])=[CH:35][CH:36]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53759827HCID 53759827, compound

Product 1

HCID 220085612-[4-(4-acetylbenzyl)-3,5-dichlorophenyl]-4,5-dihydro-1,2,4-triazin-3(2H)-oneYield 48.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In 7 ml of ethyl acetate was dissolved 0.7 g of 2-[4-(4-acetylbenzyl)-3,5-dichlorophenyl]-1-benzylidene-4-(2,2-dimethoxyethyl)semicarbazide. To the solution was added 0.27 g of 35% hydrochloric acid. The mixture was stirred for one hour at room temperature. The reaction mixture was washed with water, dried and concentrated. The residue was purified by column chromatography (Merck Silica Gel 60; normalhexane-ethylacetate=1:3) to provide 0.24 g of the title compound. m.p. 189-190° C.

Workup

  1. washThe reaction mixture was washed with water
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (Merck Silica Gel 60; normalhexane-ethylacetate=1:3)

Sources & evidence

ORD record
ord-7e7fc597874247dfadaade19834fcd8c
Source dataset
uspto-grants-1999_11
Patent number
US05994355

Reaction notes

Loading…