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1-(6'-Methoxycarbonyl-n-hex-2-enyl)-4-methyl-1,2,4-triazolidine-3,5,-dione → Methyl 7-(4-methyl-3,5-dioxo-1,2,4-triazolidin-1-YL)heptanoate

HRID 1462391
Notes
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Reaction equation

HRID 1462391 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH2:7][CH:8]=[CH:9][CH2:10][N:11]1[C:15](=[O:16])[N:14]([CH3:17])[C:13](=[O:18])[NH:12]1)=[O:4].[H][H]>C(COC)OC.[Pd]>[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:15](=[O:16])[N:14]([CH3:17])[C:13](=[O:18])[NH:12]1)=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 538819771-(6'-Methoxycarbonyl-n-hex-2-enyl)-4-methyl-1,2,4-triazolidine-3,5,-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 12953298Methyl 7-(4-methyl-3,5-dioxo-1,2,4-triazolidin-1-YL)heptanoateYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 80711,2-Dimethoxyethane
Solvent

Procedure

The 1-(6'-methoxycarbonyl-n-hex-2-enyl)-4-methyl-1,2,4-triazolidine-3,5-dione (12.4 g, 0.0486 mol) was dissolved in dimethoxyethane (200 ml) and 10% palladium on charcoal (3 g) was added and the resultant mixture was allowed to take up hydrogen (ca. 1100 mls). After the reaction was complete the resultant mixture was filtered through a kieselguhr bed and the filtrate evaporated in vacuo to afford 1-(6'-methoxycarbonyl-n-hexyl)-4-methyl-1,2,4-triazolidine-3,5-dione (12.3 g).

Workup

  1. filtrationwas filtered through a kieselguhr bed
  2. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-3ab88e4d95854b9c91715b8c56499ce5
Source dataset
uspto-grants-1984_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04460595

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes