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

HRID 321992Notes

Reaction equation

HRID 321992 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-5f5995df1583463da8ed867b9348e8e2
Source dataset
uspto-grants-2001_04
Patent number
US06211178B1

Reaction notes

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