Hydrochloric Acid → HCID 67083770, compound

HRID 2239518Notes

Reaction equation

HRID 2239518 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[N:9][CH:10]([C:14]#[N:15])[C:11]([NH2:13])=[O:12])=[CH:4][C:3]=1[O:16][CH3:17].Cl>C1(C)C=CC=CC=1.Cl[Ti](Cl)(Cl)Cl>[NH2:15][C:14]1[C:6]2[C:5](=[CH:4][C:3]([O:16][CH3:17])=[C:2]([Br:1])[CH:7]=2)[N:8]=[N:9][C:10]=1[C:11]([NH2:13])=[O:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86626060HCID 86626060, compound

Product 1

HCID 67083770HCID 67083770, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of 2-((4-bromo-3-methoxyphenyl)diazenyl)-2-cyanoacetamide (Method 12) (34.4 g, 115.8 mmol) in toluene (250 ml) under N2 was added TiCl4 (51.1 ml, 463 mmol). The reaction mixture was stirred at reflux for 4 hours before being allowed to cool to room temperature. The reaction mixture was carefully poured over an ice cold solution of 3N HCl (˜600 ml), the mixture was then allowed to warm to rt, and was then stirred at 90° C. for 10 minutes. A precipitate formed which was collected via vacuum filtration, washed with water (˜200 mL), ethanol (˜200 mL), ether (˜200 mL), and dried in vacuo to yield the title compound as a brown solid which was used without further purification (30.0 g, 87%). 1H NMR: 10.30 (s, br, 1H), 9.95 (s, br, 1H), 9.15 (s, 1H), 8.55 (s, 1H), 8.09 (s, 1H), 7.68 (s, 1H), 4.15 (s, 3H); m/z 298.

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureto warm to rt
  3. stirringwas then stirred at 90° C. for 10 minutes
  4. customA precipitate formed which
  5. filtrationwas collected via vacuum filtration
  6. washwashed with water (˜200 mL), ethanol (˜200 mL), ether (˜200 mL)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-67bdab6818fc43d7a1acc0fb07fb25ad
Source dataset
uspto-grants-2010_05
Patent number
US07723337B2

Reaction notes

Loading…