ethyl N-((7-chloro-2,3-dihydro-2-methyl-4-benzofuranylhydrazono)cyanoacetyl)carbamate → 2-(7-Chloro-2,3-dihydro-2-methyl-4-benzofuranyl)-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carbonitrile

HRID 344599Notes

Reaction equation

HRID 344599 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][CH:8]([CH3:11])[CH2:7][C:6]=2[C:5]([NH:12][N:13]=[C:14]([C:23]#[N:24])[C:15]([NH:17][C:18](=O)[O:19]CC)=[O:16])=[CH:4][CH:3]=1>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[C:10]2[O:9][CH:8]([CH3:11])[CH2:7][C:6]=2[C:5]([N:12]2[C:18](=[O:19])[NH:17][C:15](=[O:16])[C:14]([C:23]#[N:24])=[N:13]2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86743513ethyl N-((7-chloro-2,3-dihydro-2-methyl-4-benzofuranylhydrazono)cyanoacetyl)carbamate

Product 1

HCID 542357422-(7-Chloro-2,3-dihydro-2-methyl-4-benzofuranyl)-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 12.5 g of 32B and 600 mL of xylene was stirred at reflux temperature overnight under a Soxhlet extractor filled with 4A molecular sieves to collect the alcohol that was formed. The mixture was cooled to room temperature and filtered; the solid product was dried under reduced pressure to give 2-(7-chloro-2,3-dihydro-2-methyl-4-benzofuranyl)-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carbonitrile (32C) as a tan solid, m.p.: 244°-245° C.

Workup

  1. temperatureat reflux temperature overnight under a Soxhlet extractor
  2. customto collect the alcohol that
  3. customwas formed
  4. filtrationfiltered
  5. customthe solid product was dried under reduced pressure

Sources & evidence

ORD record
ord-45234c2b28e548e9a84cec8bada1e690
Source dataset
uspto-grants-1991_10
Patent number
US05053071

Reaction notes

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