Hydrochloric Acid → HCID 70616810, compound

HRID 1077259Notes

Reaction equation

HRID 1077259 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1Br.[Mg].C(Br)C.II.[CH:16](OCC)(OCC)OCC.[ClH:26].Cl.Cl.[NH2:29][N:30]1[CH:34]=[N:33][N:32]=[C:31]1[NH:35][NH2:36]>CCOCC.C(O)C.O>[ClH:26].[NH2:29][N:30]1[CH:34]=[N:33][N:32]=[C:31]1[NH:35][N:36]=[CH:16][C:3]1[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:8]

Participants

11

Reactant 7

HCID 313Hydrochloric AcidHCID 807IodineHCID 6332Ethyl BromideHCID 31214Ethyl orthoformateHCID 684712-Bromo-m-xyleneHCID 5462224MagnesiumHCID 13931004HCID 13931004, compound

Product 1

HCID 70616810HCID 70616810, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

In an atmosphere of dry nitrogen, a solution of 9.25 g (0.05 mole) of 2,6-dimethylbromobenzene in 100 ml of ether was added dropwise with stirring to 1.2 g (0.05 g atom) of magnesium turnings in 20 ml of ether. The reaction was started by the addition of ethyl bromide and a crystal of iodine. When all the halide had been added, the solution was refluxed for 2 hours. 8.2 ml (0.052 mole) of triethyl orthoformate was added dropwise and the reaction mixture was refluxed for 1.5 hour and left overnight at room temperature. To the solution was added dropwise while stirring and cooling a mixture of 50 ml of concentrated hydrochloric acid and 50 ml of water. The stirring was continued for 30 minutes. The ether layer was separated and the ether removed by evaporating. To the residue was added a solution of 9.35 g (0.05 mole) 4-amino-3-hydrazino-1,2,4-triazole dihydrochloride in 130 ml of 75 percent ethanol. The mixture was stirred and heated at reflux for 5 hours. 600 ml of ethanol was added and the solution cooled. After filtration and evaporation of the solvent 3.6 g of the crude salt was obtained. After recrystallization from ethanol-2N hydrochloric acid, the product melts at 219°-220° (D).

Workup

  1. temperaturethe solution was refluxed for 2 hours
  2. temperaturethe reaction mixture was refluxed for 1.5 hour
  3. additionTo the solution was added dropwise
  4. temperaturecooling
  5. waitThe stirring was continued for 30 minutes
  6. customThe ether layer was separated
  7. customthe ether removed
  8. customby evaporating
  9. stirringThe mixture was stirred
  10. temperatureheated
  11. temperatureat reflux for 5 hours
  12. temperaturethe solution cooled
  13. filtrationAfter filtration and evaporation of the solvent 3.6 g of the crude salt
  14. customwas obtained
  15. customAfter recrystallization from ethanol-2N hydrochloric acid

Sources & evidence

ORD record
ord-94131e8f6ae7485e88345f99ef6bd436
Source dataset
uspto-grants-1976_05
Patent number
US03959476

Reaction notes

Loading…