1,2-Dimethoxyethane → HCID 14625405, compound

HRID 1639003Notes

Reaction equation

HRID 1639003 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13][CH2:12][NH:11]1)([O-])=O.[CH3:23][O:24]CCOC>[Pd]>[C:17]1([N:14]2[CH2:15][CH2:16][N:10]3[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[NH:1][C:23](=[O:24])[N:11]3[CH2:12][CH2:13]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 80711,2-DimethoxyethaneHCID 14625401HCID 14625401, compound

Product 1

HCID 14625405HCID 14625405, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Hexahydro-1-(2-nitrophenyl)-5-phenyl-1H-1,2,5-triazepine (10.0 g) in 1,2-dimethoxyethane (500 ml) was hydrogenated over 10% palladium on carbon (2 g) at atmospheric pressure and room temperature until theoretical uptake was achieved. The mixture was filtered through Celite and the filter pad was washed with 1,2-dimethoxyethane. The filtrate was evaporated to approximately 100 ml and 1,1'-carbonyl-diimidazole (11 g) was added. The mixture, protected from moisture, was swirled and heated under reflux on a steam bath for 4 hours. The solution was evaporated to dryness. The residue in chloroform was applied to a column (75×5.4 cm) of dry column grade neutral alumina prepacked in chloroform. Elution was with chloroform and monitoring of fractions was by t.l.c. on Alox-25 uv254 plates (Brinkmann) with chloroform-methanol (9:1) as developer. The fractions containing the major component were evaporated to dryness and the residue was crystallized from chloroform-ether; wt. 7.45 g (75%), mp=196°198°. Three crystallizations from the same solvent system gave titled product, mp=198°-199°.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe filter pad was washed with 1,2-dimethoxyethane
  3. customThe filtrate was evaporated to approximately 100 ml and 1,1'-carbonyl-diimidazole (11 g)
  4. additionwas added
  5. temperatureheated
  6. temperatureunder reflux on a steam bath for 4 hours
  7. customThe solution was evaporated to dryness
  8. washElution
  9. additionThe fractions containing the major component
  10. customwere evaporated to dryness
  11. customthe residue was crystallized from chloroform-ether
  12. customwt. 7.45 g (75%), mp=196°198°
  13. customThree crystallizations from the same solvent system

Sources & evidence

ORD record
ord-6711c157a0f94b32b07ddcbac214afa5
Source dataset
uspto-grants-1989_11
Patent number
US04882323

Reaction notes

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