Triethylamine → HCID 18696614, compound

HRID 1870548Notes

Reaction equation

HRID 1870548 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[NH2:13])=[CH:5][CH:4]=1.[O:14]=[C:15](Cl)OC(Cl)(Cl)Cl.C(N(CC)CC)C>O1CCOCC1>[N:13]([C:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2)[CH:7]=[CH:8][CH:9]=1)=[C:15]=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 2358177-Methoxynaphthalen-1-amine

Product 1

HCID 18696614HCID 18696614, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the title compound of Step B (5.0 g) in p-dioxane (115 mL) at room temperature was added via syringe diphosgene (4.2 mL) followed by the addition of triethylamine (4.8 mL). The mixture was heated at reflux overnight while stirring. The reaction was monitored by IR (2267 cm-1). The reaction mixture was filtered and the residue was washed with diethyl ether. The filtrate was concentrated under reduced pressure to give 5.8 g of the title compound of Step C as a beige solid which was used without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. filtrationThe reaction mixture was filtered
  4. washthe residue was washed with diethyl ether
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e1fa4b77499c46b79bb89aedc7bde578
Source dataset
uspto-grants-2000_08
Patent number
US06096895

Reaction notes

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