Hydrazine hydrate (1:1) → N-{1-[3-(4-Methylbenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}acetamide

HRID 890691

Reaction equation

HRID 890691 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH2:12])=[NH:11])=[CH:5][CH:4]=1.O.[NH2:14]N.[C:16]([NH:19][CH:20]([CH3:28])[C:21](=O)[C:22](OCC)=[O:23])(=[O:18])[CH3:17]>C(O)C>[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]2[NH:12][C:22](=[O:23])[C:21]([CH:20]([NH:19][C:16](=[O:18])[CH3:17])[CH3:28])=[N:14][N:11]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 13430819Benzeneethanimidamide, 4-methyl-, hydrochloride (1:1)HCID 22245807Ethyl 3-acetamido-2-oxobutanoate

Product 1

HCID 135697912N-{1-[3-(4-Methylbenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 g (54.2 mmol) of 2-(4-methylphenyl)ethanamidine hydrochloride (Example 3A) are taken up in 100 ml of ethanol and treated with 3.25 g (65.0 mmol) of hydrazine hydrate. The mixture is stirred for 45 min, then the compound of Example 6A is added. It is then stirred for 4 h at 80° C. (bath) and overnight at room temperature. The substance is purified by flash chromatography, preliminary fractions first being separated off using ethyl acetate. The product is eluted with dichloromethane/methanol 30/1.

Workup

  1. stirringIt is then stirred for 4 h at 80° C. (bath) and overnight at room temperature
  2. customThe substance is purified by flash chromatography, preliminary fractions
  3. customfirst being separated off
  4. washThe product is eluted with dichloromethane/methanol 30/1

Sources & evidence

ORD record
ord-c9a112bf58034991869e037381cd0f8a
Source dataset
uspto-grants-2006_02
Patent number
US06998402B2

Linked notes

Loading…